1,1-BIS(BENZENESULFONYL)ETHYLENE: A SYNTHETIC EQUIVALENT OF ETHYLENE 1,2-DIPOLE

Article abstract of DOI:10.1016/S0040-4039(01)91097-4

1,1-Bis(benzenesulfonyl)ethylene (1) acts as a synthetic equivalent of ethylene 1,2-dipole as it gives with olefins products derived from a postulated dipolar reaction mechanism that can be readily desulfonylated into the formal ethylene adducts.

Full text of DOI:10.1016/S0040-4039(01)91097-4

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REFERENCES AND NOTES
For example benzene vinyl sulfone
853) and and
in press) have been shown to be reactive ethylene equivalents for ground state
R.V.C.; Paquette, L.A. J. Am. Chem.
1980,
1.
Pasquato, L.
Chim.
(De Lucchi 0.;
ethylene substitutes for
4184).
cycloadditions and vinyl sulfides are known as
additions (Vanderhoek, J.Y. J. Org. Chem. 1969,
2.
3.
Steinbeck, K. Liebigs Ann. Chem. 1974, 1315.
Stetter, H.;
'H-NMR
1.17-1.40
1.52-2.18
mp
3: 80% yield;
AB system split in d,
diastereotopic CH
2.33
1.96 (partially hidden) and 2.53
4.99
7.86-8.0
H ,
J
15.3) 3.09
9.2 and 3.7) 7.49-7.76,
6 5
4.
5.
Fatutta, S.; Risaliti, A. J. Chem.
P. I 1974, 2387.
'H-NMR
1.70
2.81
6.1) 3.71
mp
4:
85% yield,
4.52
6.1) 6.04
7.53-7.76, 7.92-7.99
6.
7.
8.
"Normal" Diels-Alder reactions of
Analytical and spectral data of compound
1
are published separately
Chim. It., in press).
6
are published in ref. 6.
'H-NMR
2.80
1.43, 2.25
3.7) 3.07
H , AB pattern, J
3.44
5% yield;
mp
9.5)
9:
2.28
9
3.0) 6.31
3.4) 7.48-7.74,
6.16
5.5; Jl
ml-
9.
Caple, R. J. Org. Chem. 1966,
585.
Cristol, S.J.;
'H-NMR
1.81
7.04-7.18
'H-NMR
10.4) 2.33
7.44-
7:
mp
10.
50% yield;
7.0) 2.83-2.95
7.97-8.04
3.32
3.83
8: 10% yield; oil;
3.58 4.27
pattern) 7.51-7.98
7.76,
H
6891 and
5.0) 2.94
J
7.0,
J
5
oil;
'H-NMR
2.55
D
1.10
2.60
1.21
2.93
1.90
5.62
2.26
11.
12:
70% yield,
2.30
3.0) 6.94-7.04,
5.8,
1
3.0) 5.72
Schlosberg, S.B.;
Seyferth, D.; Yamazaki, H.; Alleston, D.L. J. Org. Chem. 1963,
via cycloaddition of benzene
J. Org. Chem. 1968,
2175.
703.
12.
13.
14.
P.E.
vinyl
sulfone to
not be obtained
12 could
quadricyclane.
Tetrahedron Lett.
1980,
3339; Hwu, J.R. J. Org. Chem. 1983,
15.
Little,
Myong, S.O.
4432.
16.
17.
P.D. Tetrahedron 1977,
2019.
Adam,
Erden, I. J. Am. Chem.
1980,
4806;
A.R.;
De Lucchi, 0.;
Paquette, L.A. J. Org. Chem. 1978,
4522.
Snider,
18.
19.
B.B.; Rodini, D.J.; Conn, R.S.E.; Sealfon, S. J.
Chem.
1052.
1979,
5283.
Trost, B.M.;
J.; Burks. J. J. Am. Chem.
1983,
(Received in UK
9 May 1984)