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An unusual and efficient reaction of 2-methylene-3-phenyloxetane in the presence of lithium and 4,4′-di-tert-butylbiphenyl in THF

✍ Scribed by Mehrnoosh Hashemzadeh; Amy R Howell

Book ID: 104209982
Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 116 KB
Volume: 41
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)00060-5

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✦ Synopsis

When 2-methylene-3-phenyloxetane (4) was treated with excess lithium and DTBB (cat.), lactone 6 was isolated as an unexpected product in high yield. It is postulated that 6 arises from a coupling of a radical enolate derived from 4 and the enolate of acetaldehyde, a product of THF decomposition under the reaction conditions.

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