A ++4> POLAR CYCLOADDITION OF α-CHLOROSULFIDES WITH CONJUGATED DIENES: ONE-POT SYNTHESIS OF 1-ACYL- AND 1-CYANO-1-METHYLTHIO-2-VINYLCYCLOPROPANES

DOI: 10.1016/S0040-4039(01)81403-9

Source and publish data:

Tetrahedron Letters p. 4231 - 4232 (1984)

Update date:2022-08-05

Topics:

Authors:

Ishibashi, H.

Kitano, Y.

Nakatani, H.

Okada, M.

Ikeda, M.

et al. et al.

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Article abstract of DOI:10.1016/S0040-4039(01)81403-9

In the presence of SnCl4, methoxycarbonyl-, acetyl-, benzoyl-, or cyano-substituted chloromethyl methyl sulfide (1-4) undergoes <2⁺+4> polar cycloaddition with conjugated dienes to afford the cycloadducts of type 7, which, on treatment with base, are converted into the 1-acyl- or 1-cyano-1-methylthio-2-vinylcyclopropanes 9-10 via the ylide intermediates of type 8.

Full text of DOI:10.1016/S0040-4039(01)81403-9

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