2-Amino-1,2,3-triazole derivatives

Article abstract of DOI:10.1023/A:1009582129822

The syntheses and structure of 2-triarylphosphoranimine-1,2,3-triazole derivatives from vicinal diazides have been investigated. Compounds derived from dichloronapththoquinone, 2,3-dichloro-5,6-dimethylbenzoquinone, and 2,3,5,6-tetrachlorobenzoquinone are included. X-ray structures, NMR, IR, UV, and cyclic voltammetry data are reported. Compound 2 crystallizes in space group P1 with a = 12.31(1), b = 12.469(3), c = 10.088(3) A, a = 97.19(3), β = 103.79(6), γ = 101.84(4)^o, and D_calc = 1.466 g/cm for Z = 2. Compound 4 crystallizes in space group P2¹l c with a = 9.044(2), b = 10.882(2), c = 19.110(4) A, β = 99.06(2)^o, and D_calc = 1.324 g/cm for Z = 2. Compound 6 crystallizes in space group P2₁/a with a = 8.85(1), b = 14.841(8), c = 11.372(8) A, β = 107.19(3)^o, and D_calc = 1.397 g/cm for Z = 4. Compound 11 crystallizes in space group P2₁/n with a = 8.823(3), b = 16.501(6), c = 16.221(3) A, β = 103.58(2)^o, and D_calc = 1.309 g/cm for Z = 4. Compound 12 crystallizes in space group P1 with a = 11.606(8), b = 11.671(5), c = 10.734(3) A, α = 101.62(3), β = 93.70(4), γ = 64.33(4)^o, and D_calc = 1.438 g/cm for Z = 2. Compound 13 crystallizes in space group C2/c with a = 13.337(7), b = 9.217(6), c = 24.78(1) A, β = 102.85(5)^o, and D_cale = 1.478 g/cm for Z = 8.

Full text of DOI:10.1023/A:1009582129822

Journal of Chemical Crystallography, Vol. 29, No. 8, 1999
2-Amino-1,2,3-triazole derivatives
Satish G. Bodige,(1) Miguel Mendez-Rojas,(1) and William H. Watson(1)*
Received January 27, 1999
Thesynthesesandstructureof2-triarylphosphoranimine-1,2,3-triazolederivativesfromvicinal
diazides have been investigated. Compounds derived from dichloronapththoquinone, 2,3-
dichloro-5,6-dimethylbenzoquinone,and2,3,5,6-tetrachlorobenzoquinoneareincluded.X-ray
structures, NMR, IR, UV, and cyclic voltammetry data are reported. Compound 2 crystallizes
˚
in spacegroup P1ළ witha ϭ 12.31(1), bϭ 12.469(3), cϭ 10.088(3) A, Ͱ ϭ 97.19(3), ͱϭ 103.79(6),
Ͳ ϭ 101.84(4)Њ, and Dcalc ϭ 1.466 g/cm for Z ϭ 2. Compound 4 crystallizes in space group P21/
˚
c with a ϭ 9.044(2), b ϭ 10.882(2), c ϭ 19.110(4) A, ͱ ϭ 99.06(2)Њ, and Dcalc ϭ 1.324 g/cm for
Z ϭ 2. Compound 6 crystallizes in space group P21/a with a ϭ 8.85(1), b ϭ 14.841(8), c ϭ
˚
11.372(8) A, ͱ ϭ 107.19(3)Њ, and Dcalc ϭ 1.397 g/cm for Z ϭ 4. Compound 11 crystallizes in
˚
space group P21/n with a ϭ 8.823(3), b ϭ 16.501(6), c ϭ 16.221(3) A, ͱ ϭ 103.58(2)Њ, and Dcalc
ϭ 1.309 g/cm for Z ϭ 4. Compound 12 crystallizes in space group Pළ1 with a ϭ 11.606(8), b ϭ
˚
11.671(5), c ϭ 10.734(3) A, Ͱ ϭ 101.62(3), ͱ ϭ 93.70(4), Ͳ ϭ 64.33(4)Њ, and Dcalc ϭ 1.438 g/cm
for Z ϭ 2. Compound 13 crystallizes in space group C2/c with a ϭ 13.337(7), b ϭ 9.217(6), c ϭ
˚
24.78(1) A, ͱ ϭ 102.85(5)Њ, and Dcale ϭ 1.478 g/cm for Z ϭ 8.
KEY WORDS: 2-Triarylphosphineimino-1,2,3-triazoles; 2-triarylphosphanylideneamino-1,2,3-triazoles;
2-amino-1,2,3-triazoles; vicinal diazide reactions; X-ray structures; benzoquinone; naphthoquinone;
2,3,5,6-tetrachlorobenzoquinone.
Introduction
to moisture. The room temperature reactions of the
vicinal diazides of five-membered rings such as malei-
The reactions of quinone vicinal diazides with
mide in polar solvents lead predominately to the di-
Staudinger product;6, 7 however, the 2-amino-1,2,3-
triazole system is formed at higher temperatures.1
The reaction of o-bis-azidobenzene is reported to
give only the di-Staudinger product1 which indicates
the quinone functionality is important in the selective
formation of the triazole system.
Scheme 1 outlines the synthetic pathways used to
synthesize the compounds in this report. Compound 2
was prepared using tri-p-chlorophenylphosphine.
The reaction of the tetra-azide of 3 with triphenylpho-
sphine proceeded smoothly to give the bis-product
4. Compound 4 was hydrolyzed to give 5 which upon
sitting in acetone overnight forms 6. We had reported
previously that the free amines did not react readily
with ketones, but now find this statement to be incor-
rect. Compound 6 was insoluble in most common
solvents, and only poorly formed crystals could be
triarylphosphines give the substituted 2-triarylpho-
sphoranimine-1,2,3-triazole system.1–3 The triazole
system is formed exclusively in polar solvents such
as methanol and ethanol, but di-Staudinger products
(phosphine imides) become significant in nonpolar
solvents. The 2-aminotriazole system also has been
prepared by amine transfer reactions,4 and by a pho-
tochemical procedure.5 The quinone triazole com-
pounds are thermally stable, have sharp melting
points, and the molecular ion is frequently the major
peak in the mass spectrum. The compounds hy-
drolyze to the corresponding 2-amino-1,2,3-triazole
system upon exposure to acids or prolonged exposure
(1) Department of Chemistry, Texas Christian University, Box
298860, Fort Worth, TX 76129.
* To whom correspondence should be addressed.
931
1074-1542/99/0800-0931$16.00/0  1999 Plenum Publishing Corporation

932
Bodige, Mendez-Rojas, and Watson
obtained. Compound 7 was dibrominated in two steps
and compounds 11 and 12 were prepared from the
corresponding diazides.
AFC-6S diffractometer using the ␪-2␪ mode at a
fixed scan rate with multiple scans for weak reflec-
tions. The scan width and rate were determined
by scanning several strong reflections prior to data
collection. The data were corrected for Lorentz-
polarization effects and ⌿-scan absorption correc-
tions were applied. The data were corrected for
secondary extinction and each data set was checked
for decay of reference intensities. The structures
were solved using SIR92,9 and refined and analyzed
using TEXSAN10 and PLATON.11 Table 1 contains
crystal data, collection parameters and refinement
criteria for compounds 2, 4, 6, 11, 12, and 13
while Tables 2–7 give atomic coordinates for these
compounds. Figure 1 is a packing diagram of com-
pound 2 while Figs. 2–6 are thermal ellipsoid plots
of the remaining compounds.
Compound 2
Compound 13 was prepared in low yield from
the free amine and phathalic dicarboxaldehyde and
only the X-ray data are reported.
2,3-Dichloronaphthoquinone (1) 0.500 g (2.20
mmol) was dissolved in 20 mL of absolute ethanol
and 0.286 g (4.40 mmol) of sodium azide was added.
The solution turned orange and was stirred at room
temperature for 1h. Tri(4-chlorophenyl) phosphine
(0.805 g, 2.20 mmol) was added slowly and nitrogen
was evolved vigorously. The reaction was stirred for
more than 1 h and a dark violet solid was recovered
by vacuum filtration (1.27 g, 100% yield). Recrystalli-
zation from nitromethane yielded cubic-shaped crys-
tals, ȁ200ЊC (color change), m.p. 235–238ЊC.
1HNMR: ͳ, 7.26–8.21 (m, 16 aromatic protons);
IR(cmϪ1): 1678, 1578, 1560, 1508, 1481, 1466, 1452,
1391, 1350, 1223, 1182, 1111, 1088, 1059, 1034, 1014,
978, 957, 817, 756, 719, 677, 648, 590, 581, 554, 508,
421.
Experimental
Reagents were used as purchased. Melting
points were measured on a Thomas Hoover capillary
instrument and are uncorrected. IR spectra were re-
corded on a Midac Systems FTIR using KBr pellets.
1H NMR spectra were recorded on a Varian XL-
300 spectrometer with CDCl3 as solvent and TMS
as internal standard. Cyclic voltammetric data were
collected on a Model 173 PARC potentiostat coupled
to a Model 175 Universal Programmer and a BAS
CV-50W instrument using a standard three-electrode
microcell, with a Pt disk as working electrode and
copper and platinum wires as the reference and auxil-
iary electrodes. Ferrocene was added to all samples
as an internal reference.8
Compound 4
To a solution of 1.23 g (5 mmol) of tetrachloro-
1,4,-benzoquinone in 25 mL of methanol was added
All X-ray data were collected on a Rigaku

2-Amino-1,2,3-triazole derivatives
933
␪
␴
␳
␴
␪
␭
␳

934
Bodige, Mendez-Rojas, and Watson
Table 3. Atomic Coordinates and Biso/Beq for Compound 4
0.650 g (10 mmol) of sodium azide. The mixture was
stirred for 1 h at room temperature and the solution
changed from yellow to purple. Triphenylphosphine
(0.650 g, 10 mmol) was added slowly and nitrogen
was evolved. The solution was stirred for 3h. The
solvent was removed and the solid washed with water
and air-dried (0.544 g, 70% yield), color change
Atom
x
y
z
Beq
P(1)
0.12280(8)
0.5892(2)
0.3815(2)
0.2952(2)
0.2966(2)
0.2143(2)
0.5527(3)
0.4451(3)
0.3943(3)
0.0650(3)
0.1509(3)
0.1127(3)
Ϫ0.0092(4)
Ϫ0.0944(4)
Ϫ0.0570(3)
Ϫ0.0411(3)
Ϫ0.0812(3)
Ϫ0.2098(4)
Ϫ0.2989(4)
Ϫ0.2601(4)
Ϫ0.1308(3)
0.2271(3)
0.3248(3)
0.4098(3)
0.4009(4)
0.3070(4)
0.2215(3)
0.21188(7)
Ϫ0.2138(2)
Ϫ0.0392(2)
0.0614(2)
0.1343(2)
0.0841(2)
Ϫ0.1190(2)
Ϫ0.0299(2)
0.0747(2)
0.2120(2)
0.1505(3)
0.1529(3)
0.2189(3)
0.2788(3)
0.2769(3)
0.2154(3)
0.1092(3)
0.1086(3)
0.2099(4)
0.3142(3)
0.3181(3)
0.3502(2)
0.3953(3)
0.4990(3)
0.5572(3)
0.5117(3)
0.4089(3)
0.77729(3)
0.94282(9)
0.8617(1)
0.8532(1)
0.9099(1)
0.7882(1)
0.9678(1)
0.9305(1)
0.9593(1)
0.6817(1)
0.6398(1)
0.5670(1)
0.5366(1)
0.5781(2)
0.6509(1)
0.8196(1)
0.8516(1)
0.8832(2)
0.8813(2)
0.8498(2)
0.8197(1)
0.8023(1)
0.7594(1)
0.7780(2)
0.8411(2)
0.8844(2)
0.8656(2)
3.40(2)
5.99(6)
3.41(5)
3.39(5)
3.53(5)
3.94(5)
3.34(6)
2.90(6)
2.93(6)
3.34(6)
5.19(8)
5.78(9)
5.68(9)
6.6(1)
5.33(8)
3.66(6)
4.71(8)
6.5(1)
6.9(1)
6.5(1)
O(1)
N(1)
N(2)
N(3)
N(4)
C(1)
C(2)
C(3)
C(4)
C(5)
1
(ȁ300ЊC), m.p. Ͼ360ЊC (lit.1a Ͼ 360Њ C). H NMR:
ͳ, 7.26–7.89 (m, 30 aromatic protons); IR(cmϪ1): 2104,
1686, 1438, 1456, 1439, 1344, 1281, 1188, 1180, 1111,
C(6)
C(7)
C(8)
C(9)
Table 2. Atomic Coordinates and Biso/Beq for Compound 2
Atom
x
y
z
Beq
C(10)
C(11)
C(12)
C(13)
C(14)
C(15)
C(16)
C(17)
C(18)
C(19)
C(20)
C(21)
Cl(1)
0.7628(1)
0.9697(1)
1.1541(1)
0.7879(1)
0.8106(3)
0.3693(3)
0.3646(5)
0.4552(8)
0.7233(3)
0.6408(4)
0.5373(4)
0.6592(3)
0.4445(8)
0.7110(5)
0.6239(6)
0.5110(6)
0.4669(5)
0.5527(5)
0.6644(5)
0.6615(4)
0.4350(4)
0.5847(6)
0.4728(6)
0.7774(4)
0.6740(4)
0.6694(4)
0.7670(5)
0.8711(4)
0.8754(4)
0.8410(3)
0.8084(4)
0.8474(4)
0.9176(4)
0.9506(4)
0.9109(4)
0.8979(4)
1.0161(4)
1.0959(4)
1.0556(5)
0.9394(5)
0.8607(4)
0.5483(6)
0.3763(1)
1.1840(1)
0.6169(1)
0.7255(1)
1.0560(3)
0.8005(3)
0.3530(7)
0.2928(6)
0.8579(3)
0.7685(3)
0.7502(3)
0.6965(3)
0.3432(7)
1.0009(4)
1.0249(4)
0.9603(4)
0.8585(4)
0.8362(4)
0.8999(4)
1.1182(4)
0.9882(5)
1.1440(4)
1.0812(6)
0.6202(3)
0.5429(4)
0.4651(4)
0.4689(4)
0.5457(4)
0.6215(4)
0.8588(3)
0.8701(3)
0.9706(4)
1.0593(4)
1.0486(4)
0.9485(4)
0.7051(3)
0.7427(3)
0.7151(4)
0.6512(4)
0.6149(4)
0.6426(4)
0.4256(5)
Ϫ0.2668(1)
0.0832(1)
0.7392(1)
0.2546(1)
0.6794(3)
0.5500(3)
0.3059(9)
0.1698(7)
0.4583(4)
0.3774(4)
0.4025(4)
0.2743(4)
0.2612(9)
0.6522(5)
0.7260(5)
0.6914(5)
0.5784(5)
0.5086(5)
0.5419(5)
0.8330(6)
0.7648(6)
0.9054(5)
0.8717(6)
0.1070(4)
0.0394(5)
Ϫ0.0761(5)
Ϫ0.1202(4)
Ϫ0.0541(5)
0.0616(5)
0.2092(4)
0.0714(4)
0.0332(4)
0.1312(5)
0.2693(5)
0.3076(4)
0.3983(4)
0.4127(5)
0.5184(5)
0.6063(5)
0.5952(5)
0.4904(5)
0.3461(7)
6.88(4)
7.30(5)
7.68(5)
3.50(3)
6.0(1)
7.2(1)
18.5(3)
22.0(3)
3.8(1)
3.9(1)
3.9(1)
3.5(1)
10.6(3)
4.0(2)
3.8(2)
3.9(2)
4.2(2)
3.5(2)
3.4(2)
5.2(2)
5.3(2)
6.1(2)
5.9(2)
3.1(1)
4.1(1)
4.5(1)
4.2(1)
4.2(1)
3.8(1)
3.2(1)
4.1(1)
5.0(1)
4.6(1)
5.0(1)
4.5(1)
3.0(1)
3.8(1)
4.4(1)
4.5(2)
4.5(1)
4.0(1)
10.0(2)
Cl(2)
Cl(3)
P(1)
O(1)
O(2)
O(3)
O(4)
N(1)
N(2)
N(3)
N(4)
N(5)
C(1)
C(2)
C(3)
C(4)
C(5)
C(6)
C(7)
C(8)
5.01(8)
3.25(6)
4.50(8)
5.64(9)
5.77(9)
6.7(1)
5.39(9)
Table 4. Atomic Coordinates and Biso/Beq for Compound 6
Atom
x
y
z
Beq
O(1)
1.0858(3)
0.7863(4)
1.1930(4)
1.1904(4)
1.0716(4)
1.2808(4)
0.6788(4)
0.6782(4)
0.7971(4)
0.5527(4)
1.0174(5)
1.0708(4)
0.9963(4)
0.8562(5)
0.8020(5)
0.8776(4)
1.4311(5)
1.5279(5)
1.5170(5)
0.5471(5)
0.6648(5)
0.4111(5)
0.4675(2)
0.2621(2)
0.4542(2)
0.4251(2)
0.3698(2)
0.4630(2)
0.2745(2)
0.3037(2)
0.3596(2)
0.2918(2)
0.4221(2)
0.4134(2)
0.3607(2)
0.3054(3)
0.3131(2)
0.3655(2)
0.4553(3)
0.5013(3)
0.4058(3)
0.2140(3)
0.1395(3)
0.1984(3)
0.1909(2)
0.4587(3)
0.4616(3)
0.5699(3)
0.5724(3)
0.6839(3)
0.1852(3)
0.0783(3)
0.0768(3)
Ϫ0.0276(3)
0.2502(3)
0.3832(3)
0.4515(3)
0.3965(4)
0.2631(3)
0.1955(3)
0.7039(4)
0.8186(4)
0.6320(4)
Ϫ0.0809(4)
Ϫ0.0401(4)
Ϫ0.1898(4)
5.48(8)
7.6(1)
C(9)
O(2)
N(1)
N(2)
N(3)
N(4)
N(5)
N(6)
N(7)
N(8)
C(1)
C(2)
C(3)
C(4)
C(5)
C(6)
C(7)
C(8)
C(9)
C(10)
C(11)
C(12)
C(10)
C(11)
C(12)
C(13)
C(14)
C(15)
C(16)
C(17)
C(18)
C(19)
C(20)
C(21)
C(22)
C(23)
C(24)
C(25)
C(26)
C(27)
C(28)
C(29)
4.42(8)
4.19(8)
4.58(8)
5.10(9)
5.11(9)
4.48(9)
4.50(8)
5.24(9)
3.92(9)
3.50(9)
3.78(9)
4.8(1)
3.96(9)
3.46(8)
5.1(1)
7.1(1)
6.0(1)
4.7(1)
5.8(1)
5.6(1)

2-Amino-1,2,3-triazole derivatives
935
Table 6. Atomic Coordinates and Biso/Beq for Compound 12
1072, 1026, 993, 960, 852, 744, 721, 690, 671, 617, 561,
524, 509, 447.
Atom
x
y
z
Beq
Cl(1)
0.5219(1)
1.0829(2)
0.9842(1)
0.7150(1)
0.8099(3)
0.3057(3)
0.6845(3)
0.5818(4)
0.4677(3)
0.5801(3)
0.6979(5)
0.6095(5)
0.4851(5)
0.4186(5)
0.5051(5)
0.6325(4)
0.6782(5)
0.3967(5)
0.6556(4)
0.5311(4)
0.4892(4)
0.5751(5)
0.6980(5)
0.7399(4)
0.8237(4)
0.8085(4)
0.8866(6)
0.9811(5)
0.9973(5)
0.9176(5)
0.8027(4)
0.9312(4)
0.9852(4)
0.9156(5)
0.7887(5)
0.7357(4)
0.2254(1)
0.6870(2)
0.0162(1)
0.4719(1)
0.7299(3)
0.9905(3)
0.6483(3)
0.6618(3)
0.7604(3)
0.5818(3)
0.7873(4)
0.9082(4)
0.9702(4)
0.9310(4)
0.8154(4)
0.7496(4)
0.9498(5)
1.0854(4)
0.4021(4)
0.4589(4)
0.4039(4)
0.2914(4)
0.2315(4)
0.2866(4)
0.5283(4)
0.5703(4)
0.6217(5)
0.6297(5)
0.5878(5)
0.5409(5)
0.3457(4)
0.2587(5)
0.1579(5)
0.1436(4)
0.2292(5)
0.3287(4)
0.5095(1)
0.4535(1)
Ϫ0.3128(1)
0.1464(1)
Ϫ0.2028(3)
Ϫ0.0854(3)
Ϫ0.0299(3)
0.0330(3)
0.0190(3)
0.1113(3)
Ϫ0.1747(4)
Ϫ0.2247(4)
Ϫ0.2012(4)
Ϫ0.1130(4)
Ϫ0.0619(4)
Ϫ0.0912(4)
Ϫ0.3077(5)
Ϫ0.2571(4)
0.2494(4)
0.2912(4)
0.3689(4)
0.4059(4)
0.3647(4)
0.2847(4)
0.2330(4)
0.3624(4)
0.4310(4)
0.3671(5)
0.2370(5)
0.1717(4)
0.0172(4)
0.0206(4)
Ϫ0.0803(5)
Ϫ0.1850(4)
Ϫ0.1915(4)
Ϫ0.0896(4)
5.59(4)
8.68(6)
8.35(5)
3.15(3)
6.7(1)
5.7(1)
3.3(1)
3.3(1)
3.6(1)
3.6(1)
4.0(1)
4.1(1)
4.0(1)
3.9(1)
3.3(1)
3.0(1)
7.2(2)
6.0(2)
2.9(1)
3.4(1)
4.1(1)
3.5(1)
4.4(1)
4.5(1)
3.1(1)
4.3(1)
5.2(2)
5.1(2)
5.2(2)
4.6(1)
3.1(1)
4.2(1)
5.1(2)
4.7(1)
4.2(1)
3.6(1)
Compound 5
Cl(2)
Cl(3)
P(1)
O(1)
O(2)
N(1)
N(2)
N(3)
N(4)
C(1)
C(2)
C(3)
C(4)
C(5)
C(6)
C(7)
C(8)
C(9)
C(10)
C(11)
C(12)
C(13)
C(14)
C(15)
C(16)
C(17)
C(18)
C(19)
C(20)
C(21)
C(22)
C(23)
C(24)
C(25)
C(26)
0.354 g (0.50 mmol) of 4 in 75 mL of 1 N HCl
was refluxed for 3 h After cooling the filtered solid
was washed three times with 50 mL portions of meth-
anol yielding a yellow solid (0.121 g, 60% yield), color
change (ȁ 300Њ C), m.p. Ͼ 360ЊC (lit1a m.p. Ͼ 360ЊC).
IR(cmϪ1): 3346, 3258, 3084, 1693, 1589, 1494, 1437,
1381, 1344, 1159, 1120, 1088, 1058, 1003, 906, 852,
764, 752, 721, 692, 661, 617, 540, 509, 465.
Compound 6
0.100 g (0.45 mmol) of 5 was dissolved in 50 mL
of acetone and allowed to stand overnight. Yellow
Table 5. Atomic Coordinates and Biso/Beq for Compound 11
Atom
x
y
z
Beq
P(1)
0.82399(8)
0.6849(3)
0.9676(3)
0.7979(2)
0.8708(2)
0.9247(3)
0.8957(2)
0.7477(4)
0.7743(4)
0.8443(3)
0.9041(3)
0.8804(3)
0.8048(3)
0.7166(4)
0.8703(4)
0.8901(3)
0.9561(3)
0.9945(3)
0.9658(4)
0.9018(4)
0.8650(4)
0.8938(3)
1.0323(3)
1.0896(4)
1.0104(5)
0.8742(4)
0.8155(3)
0.6137(3)
0.5266(3)
0.3663(3)
0.2910(3)
0.3760(4)
0.5358(3)
0.13916(4)
0.4687(1)
0.3629(1)
0.2998(1)
0.2400(1)
0.2572(1)
0.1640(1)
0.4441(2)
0.4976(2)
0.4716(2)
0.3865(2)
0.3352(2)
0.3608(2)
0.5829(2)
0.5240(2)
0.0361(1)
Ϫ0.0044(2)
Ϫ0.0860(2)
Ϫ0.1262(2)
Ϫ0.0860(2)
Ϫ0.0045(2)
0.1985(1)
0.2407(2)
0.2872(2)
0.2903(2)
0.2485(2)
0.2024(2)
0.1353(2)
0.2045(2)
0.2009(2)
0.1301(2)
0.0615(2)
0.0637(2)
0.15067(4)
0.0709(1)
Ϫ0.1681(1)
0.0694(1)
0.0387(1)
Ϫ0.0298(1)
0.0714(1)
0.0170(2)
Ϫ0.0527(2)
Ϫ0.1134(2)
Ϫ0.1136(2)
Ϫ0.0445(2)
0.0152(2)
Ϫ0.0490(2)
Ϫ0.1847(2)
0.1700(2)
0.1125(2)
0.1241(2)
0.1926(2)
0.2503(2)
0.2397(2)
0.2449(2)
0.2539(2)
0.3252(2)
0.3874(2)
0.3810(2)
0.3097(2)
0.1298(2)
0.1348(2)
0.1136(2)
0.0865(2)
0.0811(2)
0.1020(2)
3.22(1)
7.70(7)
7.78(8)
3.89(5)
3.40(5)
3.89(6)
3.88(6)
4.72(8)
4.82(8)
4.89(8)
4.92(8)
3.61(6)
3.70(6)
7.0(1)
O(1)
O(2)
N(1)
N(2)
N(3)
N(4)
C(1)
C(2)
C(3)
C(4)
C(5)
C(6)
C(7)
C(8)
C(9)
C(10)
C(11)
C(12)
C(13)
C(14)
C(15)
C(16)
C(17)
C(18)
C(19)
C(20)
C(21)
C(22)
C(23)
C(24)
C(25)
C(26)
7.3(1)
crystals were filtered and air-dried (79 mg, 30% yield),
color changes (ȁ189 and 200ЊC), m.p. Ͼ 360ЊC. The
compound is very insoluble and high quality single
crystals could never be obtained. 1H NMR: ͳ, 2.39
(s, 3H), 2.17 (s, 3H); IR(cmϪ1): 3343, 3248, 1705, 1628,
1487, 1429, 1375, 1263, 1065, 1043, 993, 750, 659.
3.40(6)
4.08(7)
4.67(8)
5.10(8)
5.74(9)
5.04(8)
3.45(6)
5.03(8)
6.6(1)
6.8(1)
6.2(1)
Compound 8
4.82(8)
3.36(6)
4.30(7)
5.19(8)
5.87(9)
6.22(9)
4.77(8)
4.0 g of 7 dissolved in 20 mL of acetic acid was
warmed with 1.4 mL of Br2 in 15 mL of acetic acid.
After stirring for 30 min, the red colored solution
was poured into a beaker containing 200 mL of water.
A white solid (1.35 g, 34% yield) was separated by
vacuum filtration and dried at room temperature. 1H

936
Bodige, Mendez-Rojas, and Watson
Table 7. Atomic Coordinates and Biso/Beq for Compound 13
Atom
x
y
z
Beq
O(1)
O(2)
O(3)
N(1)
N(2)
N(3)
N(4)
C(1)
C(2)
C(3)
C(4)
C(5)
C(6)
C(7)
C(8)
C(9)
C(10)
C(11)
C(12)
C(13)
C(14)
C(15)
C(16)
C(17)
C(18)
0.5900(2)
0.8788(2)
0.6644(3)
0.7332(3)
0.6536(3)
0.6078(3)
0.6236(3)
0.6565(3)
0.7338(3)
0.8082(3)
0.8169(3)
0.7422(3)
0.6662(3)
0.7316(3)
0.8006(4)
0.8728(4)
0.8763(3)
0.5423(4)
0.5004(3)
0.5350(3)
0.4937(4)
0.4167(4)
0.3814(4)
0.4227(4)
0.6108(4)
0.0471(4)
0.2234(4)
0.6537(1)
0.5434(1)
0.3215(2)
0.5028(2)
0.5041(1)
0.5471(1)
0.4601(2)
0.6299(2)
0.6522(2)
0.6231(2)
0.5697(2)
0.5499(2)
0.5767(2)
0.7025(2)
0.7243(2)
0.6954(2)
0.6460(2)
0.4610(2)
0.4187(2)
0.3697(2)
0.3342(2)
0.3460(2)
0.3932(2)
0.4295(2)
0.3523(2)
4.92(9)
5.2(1)
9.8(2)
4.0(1)
4.1(1)
3.9(1)
4.1(1)
3.8(1)
3.3(1)
3.5(1)
3.9(1)
3.5(1)
3.2(1)
4.1(1)
4.7(1)
5.0(1)
4.3(1)
3.7(1)
3.6(1)
3.9(1)
5.6(2)
5.8(2)
5.2(2)
4.4(1)
5.6(2)
Ϫ0.3355(5)
Ϫ0.0108(4)
Ϫ0.0962(4)
Ϫ0.0819(4)
Ϫ0.1931(4)
0.0846(5)
0.1986(5)
0.2456(5)
0.1814(5)
0.0665(5)
0.0230(5)
0.2610(5)
0.3676(5)
0.4148(5)
0.3535(5)
Ϫ0.2642(5)
Ϫ0.3699(5)
Ϫ0.3953(5)
Ϫ0.5048(6)
Ϫ0.5919(6)
Ϫ0.5667(6)
Ϫ0.4575(6)
Ϫ0.2964(6)
Fig. 1. Packing diagram for compound 2.
NMR: ͳ, 6.79 (s, 1 aromatic H), 5.25 (s, 1H), 5.15 (s,
1H), 2.22–2.21 (d, 3H), 2.13 (s, 3H).
mixture was stirred for 1 h at rt. with the yellow
solution changing to purple. Triphenylphosphine
(0.276 g, 5 mmol) was added slowly which was accom-
panied by the evolution of nitrogen. The solution was
stirred for 3 h, the solvent removed and the solid
washed with water and air-dried, (0.237 g, 60% yield),
Compound 9
1.35 g of 8 in 10 mL of acetic acid was reacted
with 0.4 mL of Br2 in 10 mL of acetic acid. After 30
min the dark red solution was poured into 200 mL
of water and a violet solid (1.75 g) was recovered by
filtration. 1H NMR: ͳ, 5.25 (s, 2H), 2.22–2.21 (d, 6H).
1
color change (ȁ220ЊC), m.p. Ͼ 360ЊC. H NMR: ͳ,
7.26–7.92 (m, 15H), 2.03 (s, 6H); IR(cmϪ1): 3391,
2122, 2037, 1670, 1541, 1524, 1439, 1396, 1358, 1250,
1113, 1107, 1020, 999, 968, 904, 864, 723, 694, 638,
571, 528, 509.
Compound 10
1.75 g of 9 was dispersed in 15 mL of sodium
hypochlorite (1.5% bleach) and stirred overnight.
Vacuum filtration gave a brown solid which was re-
crystallized from MeOH yielding platelets. 1H NMR:
ͳ, 2.14 (s, 6H).
Compound 12
To 0.296 g of 10 (5 mmol) in 25 mL of ethanol
was added 0.115 g of sodium azide. The yellow mix-
ture turned to red as it was stirred for 1 h at rt.
Tri(4-chlorophenyl) phosphine (0.365 g, 5 mmol) was
added slowly. The solution was stirred for 3 h, the
solvent removed and the solid washed with water
and air-dried (0.339 g, 60% yield), m.p. 272–276ЊC.
Compound 11
To 0.296 g of 10 (5 mmol) in 25 mL of ethanol
was added 0.115 g (10 mmol) of sodium azide. The

2-Amino-1,2,3-triazole derivatives
937
Fig. 2. Thermal ellipsoid drawing for compound 4. Thermal ellipsoids at the 25% probability level while H atoms are represented by
spheres of arbitrary size.
Fig. 3. Thermal ellipsoid drawing for compound 6. Thermal ellipsoids are drawn at the 25% probability level while H atoms are represented
by spheres of arbitrary size.

938
Bodige, Mendez-Rojas, and Watson
Fig. 4. Thermal ellipsoid drawing for compound 11. Thermal ellipsoids are drawn at the
25% probability level while H atoms are represented by spheres of arbitrary size.
Fig. 5. Thermal ellipsoid drawing for compound 12. Thermal ellipsoids are drawn at the
25% probability level while H atoms are represented by spheres of arbitrary size.

Fig. 6. Thermal ellipsoid drawing of compound 13. Thermal ellipsoids are drawn at the 25% probability level while H atoms are represented
by spheres of arbitrary size.
˚
Table 9. Valence Angles (A) for Compounds 2 and 13
2
13
˚
Table 8. Bond Distances (A) for Compounds 2 and 13
C(2)UC(1)UC(6)
O(1)UC(1)UC(2)
O(1)UC(1)UC(6)
C(1)UC(2)UC(3)
C(1)UC(2)UC(7)
C(3)UC(2)UC(7)
C(2)UC(3)UC(4)
C(2)UC(3)UC(8)
C(4)UC(3)UC(8)
C(3)UC(4)UC(5)
C(3)UC(4)UO(2)
O(2)UC(4)UC(5)
C(4)UC(5)UC(6)
C(4)UC(5)UN(3)
N(3)UC(5)UC(6)
C(1)UC(6)UC(5)
C(1)UC(6)UN(1)
N(1)UC(6)UC(5)
C(6)UN(1)UN(2)
N(1)UN(2)UN(3)
N(1)UN(2)UN(4)
N(3)UN(2)UN(4)
N(2)UN(3)UC(5)
N(2)UN(4)UP(1)
N(4)UP(1)UC(11)
N(4)UP(1)UC(17)
N(4)UP(1)UC(23)
C(11)UP(1)UC(17)
C(11)UP(1)UC(23)
C(22)UP(1)UC(23)
N(2)UN(4)UC(11)
N(4)UC(11)UC(12)
C(11)UC(12)UC(13)
C(11)UC(12)UC(17)
C(12)UC(13)UC(14)
C(12)UC(13)UC(18)
C(13)UC(18)UO(3)
112.6(7)
124.9(8)
122.5(8)
123.2(8)
116.2(9)
120.6(8)
122.6(8)
119.8(8)
117.6(9)
113.4(8)
122.9(3)
123.7(8)
124.3(8)
126.5(9)
109.3(7)
123.9(8)
125.8(9)
110.3(7)
101.2(6)
117.0(6)
123.7(7)
119.3(7)
102.2(6)
115.1(5)
102.6(3)
118.6(3)
114.0(3)
106.1(3)
106.3(3)
108.1(3)
—
114.2(6)
122.7(6)
123.1(6)
122.3(6)
118.4(6)
119.3(6)
122.4(6)
118.9(6)
118.7(6)
113.9(6)
123.3(6)
122.8(6)
124.4(6)
126.3(6)
109.2(6)
122.6(6)
127.4(6)
109.9(6)
101.1(5)
117.7(5)
123.5(5)
117.0(5)
102.1(5)
—
C(1)UC(2)
C(1)UC(6)
C(1)UO(1)
C(2)UC(3)
C(2)UC(7)
C(3)UC(4)
C(3)UC(8)
C(4)UC(5)
C(4)UO(2)
C(5)UC(6)
C(5)UN(3)
C(6)UN(1)
C(7)UC(9)
C(8)UC(10)
C(10)UC(8)
N(1)UN(2)
N(2)UN(3)
N(2)UN(4)
N(4)UP(1)
P(1)UC(11)
P(1)UC(17)
P(1)UC(23)
N(4)UC(11)
C(11)UC(12)
C(12)UC(13)
C(12)UC(17)
C(13)UC(14)
C(13)UC(18)
C(14)UC(15)
C(15)UC(16)
C(16)UC(17)
C(18)UO(3)
1.500(9)
1.483(9)
1.223(7)
1.393(9)
1.401(9)
1.505(9)
1.394(9)
1.455(9)
1.215(7)
1.379(9)
1.365(8)
1.359(7)
1.388(9)
1.38(1)
1.397(9)
1.361(7)
1.337(7)
1.379(6)
1.617(5)
1.818(6)
1.812(6)
1.816(6)
—
1.490(8)
1.489(8)
1.218(7)
1.417(7)
1.379(7)
1.479(8)
1.381(8)
1.462(8)
1.222(7)
1.387(7)
1.351(7)
1.350(7)
1.373(8)
1.390(8)
1.359(8)
1.349(6)
1.328(6)
1.396(7)
—
—
—
—
—
—
—
—
—
—
1.272(7)
1.450(8)
1.410(7)
1.385(8)
1.372(9)
1.494(9)
1.385(9)
1.374(9)
1.380(9)
1.210(7)
—
—
—
—
—
—
—
—
114.4(5)
121.7(6)
125.9(6)
115.9(6)
120.7(6)
121.4(7)
122.2(8)
—
—
—
—
—
—
—

940
Bodige, Mendez-Rojas, and Watson
˚
Table 10. Bond Distances (A) for Compounds
Table 11. (Continued)
4 and 6
6
4
6
4
N(1)UN(2)UN(3)
N(1)UN(2)UN(4)
N(3)UN(2)UN(4)
N(2)UN(3)UC(3)
N(2)UN(4)UC(7)
N(4)UC(7)UC(8)
N(4)UC(7)UC(9)
C(5)UN(5)UN(6)
N(5)UN(6)UN(7)
N(5)UN(6)UN(8)
N(7)UN(6)UN(8)
N(6)UN(7)UC(6)
N(6)UN(8)UC(10)
N(8)UC(10)UC(11)
N(8)UC(10)UC(12)
N(2)UN(4)UP(1)
N(4)UP(1)UC(4)
N(4)UP(1)UC(10)
N(4)UP(1)UC(16)
C(4)UP(1)UC(10)
C(4)UP(1)UC(16)
C(11)UP(1)UC(16)
116.9(8)
124.3(8)
117.2(8)
101.3(8)
113.5(9)
114(1)
129(1)
105.2(9)
115.6(8)
123.8(9)
119.8(8)
102.4(8)
115.4(8)
125.9(9)
116.3(9)
—
117.0(3)
118.5(4)
124.4(4)
101.7(3)
—
—
—
—
—
—
—
—
—
—
—
117.7(3)
101.0(2)
113.7(2)
116.7(2)
109.0(2)
108.8(2)
107.3(2)
C(1)UC(2)
C(1)UC(6)
C(1)UO(1)
C(2)UC(3)
C(2)UN(1)
C(3)UC(4)
C(3)UN(3)
C(4)UC(5)
C(4)UO(2)
C(5)UC(6)
C(5)UN(5)
C(6)UN(7)
N(1)UN(2)
N(2)UN(3)
N(2)UN(4)
N(5)UN(6)
N(6)UN(7)
N(6)UN(8)
N(4)UC(7)
C(7)UC(8)
C(8)UC(9)
N(8)UC(10)
C(10)UC(11)
C(10)UC(12)
N(4)UP(1)
P(1)UC(4)
P(1)UC(10)
P(1)UC(16)
1.45(1)
1.47(1)
1.23(1)
1.40(1)
1.33(1)
1.46(1)
1.35(1)
1.45(1)
1.25(1)
1.39(1)
1.32(1)
1.33(1)
1.31(1)
1.34(1)
1.423(9)
1.29(1)
1.34(1)
1.387(9)
1.29(1)
1.50(1)
1.47(1)
1.30(1)
1.50(1)
1.47(1)
—
1.475(6)
1.480(5)*
1.204(5)
1.374(5)
1.354(5)
—
1.354(5)
—
—
—
—
—
1.339(4)
1.341(4)
1.362(4)
—
—
—
—
—
—
—
—
—
—
—
—
—
—
—
a One position generated by center of symmetry.
1H NMR: ͳ, 7.27–7.73 (m, 12 H), 2.03 (s, 6H);
IR(cmϪ1): 3100, 1668, 1578, 1518, 1481, 1388, 1375,
1361, 1298, 1203, 1115, 1088, 1024, 1012, 970, 908,
833, 820, 758, 744, 673, 594, 560, 509, 495, 426.
1.615(4)
1.819(4)
1.797(5)
1.800(5)
—
—
—
˚
Table 12. Selected Bond Distances (A) for Com-
˚
Table 11. Valence Angles (A) for Compounds 4 and 6
pounds 11 and 12
6
4
11
12
C(2)UC(1)UC(6)
C(2)UC(1)UO(1)
C(6)UC(1)UO(1)
C(1)UC(2)UC(3)
C(1)UC(2)UN(1)
N(1)UC(2)UC(3)
C(2)UC(3)UC(4)
C(2)UC(3)UN(3)
C(4)UC(3)UN(3)
C(3)UC(4)UC(5)
C(3)UC(4)UO(2)
C(5)UC(4)UO(2)
C(4)UC(5)UC(6)
C(4)UC(5)UN(5)
C(6)UC(5)UN(5)
C(1)UC(6)UC(5)
C(1)UC(6)UN(7)
C(5)UC(6)UN(7)
C(2)UN(1)UN(2)
111.4(8)
123.9(9)
124.6(9)
124.6(9)
127.7(9)
107.8(3)
123.6(9)
109.9(8)
126.5(9)
112.3(9)
123(1)
124.5(6)
123.6(9)
128(1)
107.9(8)
124.4(8)
126.8(9)
108.8(8)
104.2(8)
109.3(4)a
124.9(4)
125.7(4)a
126.0(4)
124.5(4)
109.5(4)
124.6(4)a
109.9(4)
125.4(4)a
—
P(1)UN(4)
P(1)UC(9)
P(1)UC(15)
P(1)UC(21)
C(1)UC(2)
C(1)UC(6)
C(1)UO(1)
C(2)UC(3)
C(2)UC(7)
C(3)UC(4)
C(3)UC(8)
C(4)UC(5)
C(4)UO(2)
C(5)UC(6)
C(5)UN(3)
C(6)UN(1)
N(1)UN(2)
N(2)UN(3)
N(2)UN(4)
1.614(3)
1.801(4)
1.798(4)
1.807(4)
1.495(5)
1.467(5)
1.210(4)
1.350(5)
1.502(6)
1.499(5)
1.505(5)
1.459(5)
1.217(4)
1.366(5)
1.351(4)
1.347(4)
1.336(4)
1.338(4)
1.358(4)
1.618(6)
1.819(7)
1.791(7)
1.786(7)
1.52(1)
1.45(1)
1.201(8)
1.319(9)
1.50(1)
1.51(1)
1.51(1)
1.478(9)
1.211(8)
1.362(9)
1.366(8)
1.356(8)
1.341(7)
1.351(7)
1.384(7)
—
—
—
—
—
—
—
—
101.9(3)

2-Amino-1,2,3-triazole derivatives
941
˚
Table 13. Valence Angles (A) for Compounds 11 and 12
solvent yielded a few colorless crystals. The sample
size was insufficient for further characterization.
11
12
N(4)UP(1)UC(9)
N(4)UP(1)UC(15)
N(4)UP(1)UC(21)
C(9)UP(1)UC(15)
C(9)UP(1)UC(21)
C(15)UP(1)UC(21)
C(2)UC(1)UC(6)
C(2)UC(1)UO(1)
C(6)UC(1)UO(1)
C(1)UC(2)UC(3)
C(1)UC(2)UC(7)
C(3)UC(2)UC(7)
C(2)UC(3)UC(4)
C(2)UC(3)UC(8)
C(4)UC(3)UC(8)
C(3)UC(4)UC(5)
C(3)UC(4)UO(2)
O(2)UC(4)UC(5)
C(4)UC(5)UC(6)
C(4)UC(5)UN(3)
N(3)UC(5)UC(6)
C(1)UC(6)UC(5)
C(1)UC(6)UN(1)
C(5)UC(6)UN(1)
C(6)UN(1)UN(2)
N(1)UN(2)UN(3)
N(1)UN(2)UN(4)
N(3)UN(2)UN(4)
N(2)UN(3)UC(5)
P(1)UN(4)UN(2)
102.0(2)
114.8(2)
115.9(2)
109.5(2)
106.0(2)
108.1(2)
115.1(4)
121.8(4)
123.1(4)
122.9(4)
114.1(4)
123.0(4)
121.5(4)
123.8(4)
114.7(4)
115.3(4)
121.6(4)
123.1(4)
123.2(4)
127.0(4)
109.8(3)
122.0(4)
128.3(3)
109.7(3)
102.1(3)
116.7(3)
125.7(3)
117.6(3)
101.8(3)
119.2(2)
99.1(3)
116.5(3)
115.9(3)
109.0(3)
107.7(3)
107.8(4)
113.0(8)
122.7(8)
124.4(7)
124.5(7)
112.9(8)
122.6(8)
122.0(7)
124.3(8)
113.8(8)
113.5(7)
122.9(7)
123.6(8)
123.7(7)
124.7(8)
111.6(6)
123.3(7)
127.4(7)
109.3(6)
101.2(6)
118.7(5)
126.0(6)
115.3(6)
99.2(5)
Discussion
In all structures containing the triphenylphos-
phine moiety there are numerous inter- and intra-
molecular interactions less than the sum of van der
Waals radii. There are no voids in the structures large
enough to contain a molecule of solvent except for
compound 2 which crystallizes as a nitromethane
adduct.
In compound 2 the naphthoquinone-1,2,3-tri-
azole system is planar (␴p ϭ 0.008 A) with P(1), N(4),
˚
and phenyl ring C(1) being coplanar (interplanar
angle 4.8(3)Њ. The two remaining phenyl rings are al-
most symmetrically oriented about the extended pla-
nar system (69.9(9) and 78.9(9)Њ). Two nitromethane
molecules related by a center of symmetry occupy a
cage which is bounded by phenyl groups from two tri-
phenyl-phosphine units. The entire molecule of 13 is
˚
planar (␴p ϭ 0.082 A) due to an extended delocalized
system and a weak interaction between N(4) and
˚
H(10): N(4)иииC(18) ϭ 2.805(7) A, N(4)иииH(10) ϭ
˚
2.19 A. The N(2)UN(4)UC(11)UC(12) torsion
angle is 179.7(4), and the interplanar angle between
the naphthoquinonetriazole system (␴ ϭ 0.023 A)
and the C(12) phenyl ring (␴ ϭ 0.006 A) is 4.7(2)Њ.
118.4(5)
˚
p
˚
p
Tables 8 and 9 give bond distances and valence angles
for compounds 2 and 13.
Compound 13
Compound 4 lies on a center of symmetry. The
To 107 mg (1 mmol) of the free amine (2-amino-
2-hydrobenzo[f]benzotriazole-4,9-dione) in 30 mL
dichloromethane was added 67 mg (0.5 mmol) of
phthalic dicarboxaldehyde and the mixture refluxed
over night. After filtration a slow evaporation of the
central three-ring system is essential planar (␴ ϭ
p
˚
0.026 A) with a 2.5(1)Њ angle between the five- and
six-membered rings. N(4) and O(1) lie out of the
˚
plane by ϩ0.071 and Ϫ0.094 A. None of the triphenyl
phosphine rings are coplanar with the central plane
exhibiting interplanar angles of 26.3(1), 77.4(1), and
83.8(1)Њ. Tables 10 and 11 give bond distances and
valence angles for compounds 4 and 6.
Table 14. Ep Values for Compounds 2, 4, 5, 6, 11, and 12a
Compound 6 has a slightly bowed conformation
Anodic sweep
(Volts vs NHE)
Cathodic sweep
(Volts vs NHE)
˚
(␴ ϭ 0.020 A) with N(4) and N(8) lying Ϫ0.236(3)
Compound
p
˚
and Ϫ0.226(3) A out of the plane. O(1) and O(2) lie
2
4
5
6
11
12
Ϫ0.949, Ϫ1.248
Ϫ0.911
Ϫ0.707, Ϫ1.493
Ϫ0.902
Ϫ0.981
Ϫ0.806, Ϫ1.017
Ϫ1.201
Ϫ1.374
Ϫ0.989
Ϫ1.441, Ϫ1.065
ϩ0.268, ϩ0.831
Ϫ1.076
on either side of the central plane ϩ0.027(3) and
˚
Ϫ0.050(3) A.
The benzenetriazole rings in 11 and 12 are planar
˚
(␴ ϭ 0.017 and 0.013 A, respectively) with phenyl
p
C(9) being coplanar (interplanar angles of 4.1(2) and
5.6(2)Њ) as found in compound 2. The remaining two
phenyl groups are symmetric about this plane
(70.0(2) and 71.9(2) for 11 and 77.7(2) and 76.2(2)
a All cyclic voltammetric analyses performed at 25ЊC using CH3CN
as solvent with 0.1 M TBAP as electrolyte. All oxidation-reduc-
tions are irreversible.

942
Bodige, Mendez-Rojas, and Watson
for 12). Tables 12 and 13 give bond distances and
valence angles for compounds 11 and 12.
References
1. (a) Mosby, W.L.; Silva, M.L. J. Chem. Soc. 1965, 1003. (b)
Gangneaux, P.; Marechal, E. Bull. Soc. Chim. Fr. 1973, 1466.
2. Sun, D.; Watson, W.H. J. Org. Chem. 1997, 62, 4082.
3. Sun, D.; Krawiec, M.; Campana, C.F.; Watson, W.H. J. Chem.
Crystallogr. 1997, 27, 577.
4. (a) Campbell, rees, C.W. Proc. Chem. Soc. 1964, 296. (b)
Campbell, Rees, C.W. Chem. Comm. 1965, 192. (c) Nakazawa,
T.; Murata, I. Angew. Chem. Internat. Edit. 1986, 27,
3005.
5. Albini, A.; Bettinetti, G.F.; Minoli, G. J. Org. Chem. 1983,
48, 1080.
6. Bo¨hm, E.; Dehnicke, K.; Beck, J.; Hiller, W.; Stra¨hle, J.
Maurer, A.; Fenske, D.Z. Z. Naturforsch. 1988,
43B, 138.
Table 14 presents cyclic voltammetry data. The
reference ferrocene gives a reversible one electron
wave while all other oxidation-reductions are irre-
versible. Oxidation of 2-amino-1,2,3-benzotriazole
gave mucononirtile;4b however, the anticipated dini-
trene intermediate could not be trapped. Nitrous acid
oxidation of the triphenyl analog of 2 gave the 1H-
triazole derivative.1 The products from chemical and
electrochemical oxidation of 2-amino-benzoqui-
nonetriazoles are being investigated.
7. Bodige, S.G.; Mendez-Rojas, M.; Watson, W.H. J. Chem.
Crystallogr. 1999, 29, 57.
8. Gagne, R.R.; Koval, C.A.; Lisensky, G.C. Inorg. Chem. 1980,
19, 2854.
9. Altomare, A.; Cascarano. M.; Giacovazzo. C.; Guagliardi, A.
J. Appl. Crystallogr. 1993, 26, 343.
10. TEXSAN-TEXRAY Structure Analysis Package; Molecular
Structure Corporation, Vers. 1.7–1, March 1995.
11. Spek, A.L. Acta Crystallogr. 1982, 29, 203.
12. Beilstein nomenclature.
Acknowledgement
The thank the Robert A. Welch Foundation
(Grant P0074) for their financial support.