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A new method for exclusive α-methylenation of fused γ-butyrolactones via pyrolysis of α-phenylsulfinyl lactones

✍ Scribed by Paul A. Grieco; James J. Reap

Publisher: Elsevier Science
Year: 1974
Tongue: French
Weight: 190 KB
Volume: 15
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)82416-3

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✦ Synopsis

Work in our Laboratories has led to a number of new approaches for the construction of the a-methylene lactone structural unit employing O-hydroxymethyl,' a-carboxylic acid,2 and (II-phenylseleny13 lactones. Continued interest4 in methods for the synthesis of a-methylene lactones prompts us to report a novel CZ-methylenation procedure for conversion of the trans-fused ybutyrolactone 1 into the trans-fused CZ-methyleney-butyrolactone 5 with complete exclusion of the endocyclic isomer 6.

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