Preparation and Properties of 2-Methyleneoxetanes

…, AJ Ndakala, M Hashemzadeh, G Wang…

Index: Dollinger, Lisa M.; Ndakala, Albert J.; Hashemzadeh, Mehrnoosh; Wang, Gan; Wang, Ying; Martinez, Isamir; Arcari, Joel T.; Galluzzo, David J.; Howell, Amy R.; Rheingold, Arnold L.; Figuero, Joshua S. Journal of Organic Chemistry, 1999 , vol. 64, # 19 p. 7074 - 7080

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Citation Number: 52

Abstract

The methylenation of β-lactones 5 with dimethyltitanocene provides a versatile, reliable, and highly chemoselective entry to 2-methyleneoxetanes 7. The conversion proceeds selectively in the presence of alkenes, unprotected alcohols, and a variety of other carbonyl moieties. A study of conditions for the optimization of this reaction is delineated. In addition, the first X- ray structure of a 2-methyleneoxetane, which shows its similarity to related β-lactones, is ...