Intramolecular nucleophilic addition to unsaturated carbon. Dependence of cyclization efficiency on the method of carbon-carbon bond cleavage utilized to generate …

LA Paquette, JP Gilday…

Index: Paquette, Leo A.; Gilday, John P.; Maynard, George D. Journal of Organic Chemistry, 1989 , vol. 54, # 21 p. 5044 - 5053

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Citation Number: 22

Abstract

The following three reactions have been studied for the purpose of comparing their intrinsic ability to generate carbanionic intermediates capable of intramolecular cyclization:(a) the Haller-Bauer cleavage of ketones 15a and 15b, as well as the@)-(+)-antipode of 15a (viz. 47);(b) the base-promoted cleavage of 1, l-diarylcarbinols 16a and 16b;(c) decarboxylative elimination within the methyllithium adducts of carboxylic acids 17a and 17b. The Haller- ...