References

R.A. Silverman and D.M. Burness J. Org. Chem. 33 (1968), p. 1869. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (5)
Y.L. Danyushevski, M.A. Marakatkina and Y.L. Goldfarb Zh. Org. Khim. 6 (1970), p. 865.
A. Mosterd, H.J. Matser and H.J.T. Bos Tetrahedron Lett. (1974), p. 4179. Abstract | PDF (113 K) | View Record in Scopus | Cited By in Scopus (4)
H. Ishibashi, S. Akai, H.-D. Choi, H. Nakagawa and Y. Tamura Tetrahedron Lett. 24 (1983), p. 3877. Abstract | PDF (114 K) | View Record in Scopus | Cited By in Scopus (0)

M.V. Sargent and P.M. Dean In: A.R. Katritsky and C.W. Rees, Editors, Comprehensive Heterocyclic Chemistry 4, Pergamon Press, Oxford (1984), p. 601.

K. Inomata, S. Aoyama and H. Kotake Bull. Chem. Soc. Jpn. 51 (1978), p. 930. Full Text via CrossRef
T. Mandai, T. Moriyama, Y. Nakayama, K. Sugino, M. Kawada and J. Otera Tetrahedron Lett. 25 (1984), p. 5913. Abstract | PDF (218 K) | View Record in Scopus | Cited By in Scopus (7)

For another base catylyzed elimination of an α-chloro sulfide that is less stereoselective P. Bakuzis and M.L.F. Bakuzis J. Org. Chem. 46 (1981), p. 235 see . Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (53)

The vinyl sulfide 1 is best stored at 0° as a neat oil.

O. Ruel, Bi Ekogka C. Bibang and S.A. Julia Tetrahedron Lett. 24 (1983), p. 4829. Abstract | PDF (203 K) | View Record in Scopus | Cited By in Scopus (2)
M. Wada, H. Nakamura, T. Taguchi and H. Takei Chem. Lett. (1977), p. 345. Full Text via CrossRef

Z-Vinyl sulfides can undergo vinyl deprotonation Bi Ekogka C. Bibang, O. Ruel and S.A. Julia Tetrahedron Lett. 24 (1983), p. 4825 see .

A γ-amino group, one of the better chelating groups, does direct deprotonation α to the sulfur in vinyl sulfides J.J. Fitt and H.W. Gschwend J. Org. Chem. 44 (1979), p. 303 see . Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (10)

A typical experiment is as follows: To the vinyl sulfide 1 (800 mg, 3.85 mmoL) in DME (8 ml) at −78° was added s-BuLi(4.4 ml of a 1.3 M solution in cyclohexane, 5.7 mmoL). After warming to −40° for 15 min the reaction was recooled to −78° and dihydrocinnamaldehyde (773 mg, 5.7 mmol) was added neat. Upon warming to 0° the reaction was diluted with hexane-ether (9:1, 100 ml), washed with aqueous K₂CO₃(2 x 50 ml), dried (MgSO₄) and concentrated. The resulting yellow oil was dissolved in methanol (14 ml) and stirred in the presence of d-camphorsul tonic acid (40 mg) for 16 hr at room temperature (other examples have shown that 3 hr is sufficient to complete the reaction). Dilution with hexane (100 ml) followed by washing with 10% aqueous K₂CO₃(2 x 40 ml), drying (MgSO₄)and concentrating gave a yellow oil. This residue was purified by flash chromatography (2 x 15 cm) using ethyl acetate hexane (2:98) as the eluent to yield 6b (740 mg, 69%) as a colorless oil.

All new compounds have been fully characterized by IR, ¹H NMR and mass spectroscopy.

The cycloaddition of vinyl heterocycles is of considerable current interest W.E. Noland, C.K. Lee, S.K. Bae, B.Y. Chung, C.S. Hahn and K.J. Kim J. Org. Chem. 48 (1983), p. 2488 see . Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (7)
K. Hayakawa, Y. Mitsuaki, S. Ohsuki and K. Kanematsu J. Am. Chem. Soc. 106 (1984), p. 6735. Full Text via CrossRef | View Record in Scopus | Cited By in Scopus (33)

A. Murai, K. Takahaski, H. Taketsuru and T. Masamune Chem. Comm. (1981), p. 221. Full Text via CrossRef
P.X. Iten, A.A. Hofmann and C.H. Eugster Helv. Chim. Acta. 62 (1979), p. 2202. Full Text via CrossRef