1
882
A. V. Narsaiah, K. Nagaiah
SHORT PAPER
Table 1 Regeneration of Carbonyl Compounds with SbCl5
References:
Entry Substratea
Productb
(1) (a) Chermis, N. D.; Entrikin, J. B. Identification of Organic
Compounds; Wiley Interscience: New York, 1963.
Time
h)
Yield
(%)c
(
(
b) Barton, D. H. R.; Beaton, J. M.; Geller, L. E.; Pechet, M.
a
OH
O
2.0
92
M. J. Am. Chem. Soc 1961, 83, 4076. (c) Barton, D. H. R.;
Beaton, J. M. J. Am. Chem. Soc. 1961, 83, 4083.
2) Kabalka, G. W.; Pace, R. D.; Wadgaonkar, P. P. Synth.
Commun. 1990, 20, 2453.
3) Greene, J. G.; Wuts, P. G. M. Protecting Groups in Organic
Synthesis; Wiley: New York, 1991, 175–223.
N
MeO
MeO
MeO
H
H
H
(
(
MeO
OMe
OMe
b
OH
O
2.15
80
N
(4) Whitesell, J. K.; Whitesell, M. A. Synthesis 1983, 517; and
H
references cited therein.
O2N
O
O2N
(
5) Donaruma, L. G.; Helolt, W. Z. Org. React. 1960, 11, 1.
c
OH
3.0
80
85
(6) (a) Donaldson, R. E.; Saddler, J. C.; Byrn, S.; McKenzie, A.
T.; Fuchs, P. L. J. Org. Chem. 1983, 48, 2167. (b) Corsaro,
A.; Ugo, Ch.; Pistara, V. Synthesis 2001, 1903. (c) Habib,
F.; Jamalian, A.; Karimi, B. Bull. Chem. Soc. Jpn. 2002, 75,
1761. (d) Hangarge, R. V.; Mane, A. S.; Chavan, V. P.;
Shingare, M. S. Indian. J. Chem., Sect. B 2002, 41, 1302.
N
d
OH
O
2.30
N
H
H
(
7) (a) Curran, D. P.; Brill, J. F.; Rakiewicz, D. M. J. Org. Chem.
1984, 49, 1654. (b) Drabowicz, J. Synthesis 1980, 125.
MeO
O
MeO
(
c) Corey, E. J.; Hopkins, P. B.; Kim, S.; Yoo, S.; Nambiar,
e
f
OH
2.30
2.45
87
82
N
N
K. P.; Flack, J. R. J. Am. Chem. Soc. 1979, 101, 7131.
H
H
(8) (a) Chrisman, W.; Blankinship, M. J.; Taylor, B.; Haris, C.
E. Tetrahedron Lett. 2001, 42, 4775. (b) Rao, C. G.;
OH
O
O
Krishna, A. H. R.; Singh, B. B.; Bhatnagar, S. P. Synthesis
1983, 808. (c) Verma, R. S.; Mesharam, H. M. Tetrahedron
CH3
CH3
Lett. 1997, 38, 5427. (d) Nattier, B. A.; Eash, K. J.; Mohan,
R. S. Syntheisis 2001, 1010. (e) Olah, G. A.; Liao, Q.; Lee,
C. S.; Prakash, G. K. S. Synlett 1993, 427. (f) Bose, D. S.;
Narsaiah, A. V. Synth. Commun. 1999, 29, 937. (g) Bose,
D. S.; Narsaiah, A. V. Synth. Commun. 2000, 30, 3121.
(h) Bose, D. S.; Narsaiah, A. V. Synth. Commun. 2000, 30,
g
h
N OH
3.0
3.0
80
75
OH
H
O
6
N
H
O
1153. (i) Khazaci, A.; Vaghei, R. G. Tetrahedron Lett. 2002,
43, 3073. (j) Shaker, S. C.; Gopalaiah, K. Tetrahedron Lett.
2002, 43, 4023. (k) Sandhu, J. S.; Boruah, A.; Boruah, B.;
6
i
j
OH
N
2.45
2.30
78
75
Prajapati, D. Tetrahedron Lett. 1997, 38, 4267.
l) Hashemi, M. M.; Beni, Y. A. Synth. Commun. 2001, 31,
95. (m) Geneste, F.; Racelma, M.; Moradpour, A. Synth.
(
2
OH
O
Commun. 1997, 27, 957. (n) Lee, J. G.; Hwang, J. P. Chem.
Lett. 1995, 507. (o) Baruah, J. B.; Sen, K. Indian J. Chem.,
Sect. A 1993, 32, 980. (p) Hajipour, A. R.; Mallakpour, S.
E.; Baltork, I. M.; Backnejad, H. Indian J. Chem., Sect. B
N
N
H
H
k
OH
O
2.0
88
2002, 41, 1302. (q) Demir, A. S.; Tanyeli, C.; Altinel, E.
H
Tetrahedron. Lett. 1997, 38, 7267.
H
(
9) (a) Laszlo, P.; Polla, S. Synthesis 1985, 439. (b) Heravi, M.
M.; Tajbakhsh, M. Phosphorus, Sulfur, Silicon Relat. Elem.
2001, 176, 195.
10) (a) Hajipour, A. R.; Mallapour, S. E.; Shoee, S. Synth.
Commun. 2002, 32, 9. (b) Varma, R. S.; Meshram, H. M.
Tetrahedron. Lett. 1997, 38, 7973. (c) Heravi, M. M.;
Ajami, D.; Mohajerani, B.; Hyder, K. T.; Mitra, G. Synth.
Commun. 2002, 32, 3325.
Cl
Cl
H
Cl
Cl
H
l
3.0
78
75
(
N
O
OH
m
2.30
H
H
O
O
N
O
OH
OH
(
(
11) Sheldon, R. A. CHEMTECH 1991, 566.
12) Olah, G. A.; Kobayashi, S.; Tashiro, M. J. Am. Chem. Soc.
1972, 94, 7448.
n
O
2.45
2.30
80
82
N
H
H
F
F
o
OH
O
N
a
All substrates were prepared by known literature procedures.
All products were characterized by comparison of their mps, IR and
H NMR spectra with those of authentic samples.
b
1
c
Yields refer to isolated pure products.
Synthesis 2003, No. 12, 1881–1882 © Thieme Stuttgart · New York