Abstract
α-Methylene-γ-hutvrolactones can be viewed as derivatives of homoallylic alcohols, potentially obtainable from rearrangements of cyclopropylcarbinyl derivatives. In order to test this concept, the cyclopropylcarbinyl derivatives 3a-7a were prepared. Acid-catalyzed rearrangements of 3a and 4a, solvolytic rearrangements of 5a, and AgC104-induced rearrangements of 6a and 7a gave the α-methylene-γ-butyrolactone 10 in good yields. The unsaturated substrates 3b-6b were similarly prepared and shown to rearrange to o-methylene lactone 16, showing that a suitably placed double bond can direct the regiochemistry of these rearrangements. Lactone 16 has a double bond in a position characteristic of many naturally occurring lactones.
Original language | English (US) |
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Pages (from-to) | 786-793 |
Number of pages | 8 |
Journal | Journal of Organic Chemistry |
Volume | 44 |
Issue number | 5 |
DOIs | |
State | Published - 1979 |
Externally published | Yes |
ASJC Scopus subject areas
- Organic Chemistry