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 language | English (US) |
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Pages (from-to) | 2220-2226 |
Number of pages | 7 |
Journal | Journal of Organic Chemistry |
Volume | 53 |
Issue number | 10 |
DOIs | |
State | Published - May 1 1988 |
All Science Journal Classification (ASJC) codes
- Organic Chemistry