N. Kamigata et al.rJournal of Organometallic Chemistry 552 (1998) 39–43
43
1
Mq
1
670, 1600, 1570, 1220, 1100, and 920 cmy1; H NMR
Hz
.
; MS
Ž
mrz
8
.
172
Ž
.
, 137, 124, and 96. HRMS:
Ž
400 MHz, CDCl3
Hz
Hz
.
d 7.17
, and 7.96
100 MHz, CDCl3
Ž
2H, dd, Js8.8 and 8.8
2H, dd, Js8.8 and 5.4
d 116.4, 124.1,
mrz 218
, 123, and 95. Anal. Calcd for C H OFCl :
Calcd for C H OFCl, 172.0091. Found: mrz 172.0075.
6
.
, 7.22
;
Ž
1H, s
.
Ž
4-Chlorophenacyl chloride
Ž
4e
400 MHz, CDCl3
2H, d, Js8.6 Hz , and 7.91
.
: mp 96.8–97.68C
1
3
1
.
C NMR
Ž
.
Ž
Ž
102–1038C w24x
2H, s , 7.48
; MS mrz 188 M , Cl , 141, and 111.
Ž . Ž .
.
; H NMR
Ž
.
d 4.66
1
31.5, 133.6, 136.0, 166.4, and 185.5; MS
Ž
.
.
Ž
.
35
Ž
2H, d,
q
35
q
Ž
M , Cl
.
Js8.6 Hz
.
9
5
2
C, 49.35; H, 2.36. Found: C, 48.81; H, 2.11. HRMS:
Calcd for C H OFCl , 217.9701. Found: mrz
9
5
2
2
17.9710.
X
References
3
,3-Dichloro-1-
Ž
4 -chlorophenyl
.
propen-1-one
Ž
2e
.
.
:
;
colorless needles; mp 49.1–49.98C
IR neat
Ž
51–528C w19,20x
y1
1
w1x N. Kamigata, H. Sawada, N. Suzuki, M. Kobayashi, Phosphorus
and Sulfur 19 Ž1984. 199.
Ž
.
3080, 1660, 1580, and 1220 cm ; H NMR
d 7.22 1H, s , 7.47 2H, d, Js8.8
2H, d, Js8.8 Hz
d 123.8, 129.5, 130.2, 135.5, 136.6,
Ž
400 MHz, CDCl3
.
Ž
.
Ž
13
w2x N. Kamigata, J. Ozaki, M. Kobayashi, Chem. Lett. Ž1985. 705.
Hz
.
, and 7.86
Ž
.
;
C NMR
Ž
100
w x
N. Kamigata, M. Kameyama, Chem. Lett. 1986 527.
Ž .
3
MHz, CDCl3
1
9
.
w4x N. Kamigata, T. Fukushima, M. Yoshida, J. Chem. Soc., Chem.
q
35
Ž
.
40.6, and 185.7; MS
5.
mrz 234 M , Cl , 141, and
Ž . Ž .
Commun. 1989 1559.
w5x N. Kamigata, T. Fukushima, Y. Terakawa, M. Yoshida, H.
Sawada, J. Chem. Soc., Perkin Trans. 1 Ž1991. 627.
w6x N. Kamigata, K. Udodaira, T. Shimizu, J. Chem. Soc., Perkin
X
3
,3-Dichloro-1-
Ž
4 -nitrophenyl
.
propen-1-one
108–1098C
2f :
Ž .
pale yellow needles; mp 109.0–109.88C
w21,22x
; IR neat 3100, 1680, 1600, 1560, 1520, 1350,
and 1220 cm ; H NMR
1H, s , 8.09 2H, d, Js8.8 Hz
Ž
Ž
.
Trans. 1 1997 783.
.
Ž
.
w7x M. Kameyama, N. Kamigata, M. Kobayashi, J. Org. Chem. 52
y1
1
Ž
1
987 3312, and references cited therein.
.
Ž
400 MHz, CDCl3
, and 8.36
100 MHz, CDCl3. d 122.6,
23.7, 129.1, 138.2, 141.2, 150.2, and 184.5; MS mrz
.
d 7.31
2H, d,
w8x N. Kamigata, J. Ozaki, M. Kobayashi, J. Org. Chem. 50 Ž1985.
Ž
.
Ž
.
Ž
1
3
5045.
Js8.8 Hz
.
;
C NMR
Ž
9
w x
N. Kamigata, K. Udodaira, T. Shimizu, Phosphorus, Sulfur and
Silicon, in press.
1
2
Ž
.
q
35
45
Ž
M , Cl
.
, 219, 164, and 151.
3a
400 MHz, CDCl3
w10x H. Matsumoto, T. Nakano, Y. Nagai, Tetrahedron Lett. Ž1973.
147.
w11x H. Matsumoto, T. Nikaido, Y. Nagai, Tetrahedron Lett. Ž1975.
99.
w12x H. Matsumoto, T. Nakano, T. Nikaido, Y. Nagai, Chem. Lett.
Phenacyl chloride
Ž
.
: mp 51.0–51.88C
Ž
.
548C w23x
, 7.50 2H,
, and
.
;
5
1
H NMR
Ž
.
d 4.67
Ž
2H, s
Ž
8
dd, Js7.3 and 7.3 Hz
.96
and 77.
-Methoxyphenacyl chloride
.
, 7.62
.
Ž
1H, t, Js7.3 Hz
.
q
7
Ž
2H, d, Js7.3 Hz
; MS
Ž
mrz
.
154
Ž
M
.
, 105,
Ž
1
.
978 115.
w13x H. Matsumoto, T. Nakano, K. Takasu, Y. Nagai, J. Org. Chem.
3 Ž1978. 1734.
4
Ž
3b : colorless needles;
.
4
w14x T.A. Stephenson, G. Wilkinson, J. Inorg. Nucl. Chem. 28
mp 97.9–98.58C
2
Ž
56–578C w23x
.
;1IR KBr 3020, 3000,
H NMR 400 MHz,
2H, s , 6.96 2H, d,
Ž
.
Ž1966. 945.
y1
950, 1700, and 1600 cm
;
Ž
w15x P.S. Hallam, T.A. Stephenson, G. Wilkinson, Inorg. Synth. 12
CDCl3
.
d 3.88
, and 7.94
100 MHz, CDCl3 d 45.3, 55.5, 113.7, 113.8, 126.9,
Ž
3H, s
.
, 4.65
Ž
.
Ž
Ž
.
1972 238.
1
3
Js5.3 Hz
.
Ž
2H, d, Js5.3 Hz
.
;
C NMR
w16x T.A. Stephenson, G. Wilkinson, J. Chem. Soc., A Ž1970. 2497.
w17x H.O. House, L.J. Czuba, M. Gall, H.D. Olmstead, J. Org.
Chem. 34 Ž1969. 2324.
Ž
.
q
1
30.6, and 189.3; MS
Ž
mrz
.
184
3c
Ž
M
.
, 135, and 77.
: mp 53.1–53.88C
d 2.43
, and 7.86
w18x S. Searles, R.A. Sanchez, R.L. Soulen, D.G. Kundiger, J. Org.
4
-Methylphenacyl chloride
Ž
.
Chem. 32 Ž1967. 2655.
1
Ž
Ž
Ž
56–578C w24x
; H NMR
400 MHz, CDCl3
. Ž .
w19x L. Zakharkin, Izu. Akad. Nauk SSSR, Otd. Khim Nauk 313
Ž1956. .
3H, s , 4.69
.
Ž
2H, s , 7.30
2H, d, Js8.0 Hz ; MS
.
Ž .
2H, d, Js8.0 Hz
q
w20x L. Zakharkin, Chem. Abstr. 50 Ž1956. 15492.
w21x R. Saulen, PhD Thesis, Kansas State Univ., 1964.
w22x R. Saulen, Dissertation Abstr. 21 Ž1960. 465.
w23x J.P. Schaefer, F. Sonnenberg, J. Org. Chem. 28 Ž1963. 1128.
.
Ž
mrz
.
168
Ž
M
.
, 119, 105,
and 91.
1
4
-Fluorophenacyl chloride 3d
Ž
.
: mp 42.7–43.68C; H
NMR d 4.67
Js8.8 and 8.8 Hz , and 8.01 2H, dd, Js8.8 and 5.1
Ž
400 MHz, CDCl3
.
Ž
2H, s
.
, 7.18
Ž
2H, dd,
w
x
24 S. Kajigaeshi, T. Kakinami, M. Moriwaki, S. Fujisaki, K.
.
Ž
Maeno, T. Okamoto, Synthesis Ž1988. 545.