Carbonyl homologation via α-trimethylsilyl β-lactone rearrangements. A nonbasic alternative to the Wittig reaction

Article abstract of DOI:10.1080/00397919508010783

Saturated and unsaturated aldehydes and ketones, when treated with trimethylsilylketene and BF₃ for 16 hours, form β-lactones which spontaneously rearrange to α,β-unsaturated TMS esters; these hydrolyze during workup to form the corresponding carboxylic acids.

Full text of DOI:10.1080/00397919508010783

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Synthetic Communications: An
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Carbonyl Homologation via
β-Trimethylsilyl β-Lactone
Rearrangements. A Nonbasic
Alternative to the Wittig
Reaction
T. Howard Black a , Yong Zhang a , Jianhua Huang a ,
Douglas C. Smith a & Bryan E. Yates a
a Department of Chemistry, Eastern Illinois
University, Charleston, Illinois, 61920
Version of record first published: 23 Sep 2006.
To cite this article: T. Howard Black, Yong Zhang, Jianhua Huang, Douglas C.
Smith & Bryan E. Yates (1995): Carbonyl Homologation via β-Trimethylsilyl β-
Lactone Rearrangements. A Nonbasic Alternative to the Wittig Reaction, Synthetic
Communications: An International Journal for Rapid Communication of Synthetic
Organic Chemistry, 25:1, 15-20
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