Internal thioaldehyde trapping by enes and dienes

E Vedejs, TH Eberlein, RG Wilde

Index: Vedejs, E.; Eberlein, T. H.; Wilde, R. G. Journal of Organic Chemistry, 1988 , vol. 53, # 10 p. 2220 - 2226

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Citation Number: 41

Abstract

Intermolecular ene insertion of photochemically generated thioaldehyde Me02CCH= S with 8-pinene occurs at room temperature to give the sulfide 2c. The internal ene insertion of thioaldehyde 6 affords a six-membered carbocycle 9 rather than the seven-membered sulfide 10 which would correspond to the regiochemistry of the intermolecular process (eq 5, 6). Likewise, internal Diels-Alder trapping occurs without a dominant role for the ...