Internal Thioaldehyde Trapping by Enes and Dienes

E. Vedejs, Thomas Eberlein, R. G. Wilde

Research output: Contribution to journalArticlepeer-review

40 Scopus citations

Abstract

Intermolecular ene insertion of photochemically generated thioaldehyde MeO2CCH=S with β-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 regiochemical preferences seen in intermolecular reactions. Desulfurization of typical internal adducts such as 25,26 or 29,30 affords 31 and 33,34, respectively.

Original languageEnglish (US)
Pages (from-to)2220-2226
Number of pages7
JournalJournal of Organic Chemistry
Volume53
Issue number10
DOIs
StatePublished - May 1 1988

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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