"Study of the Rearrangements of Oxonium Ylides Generated from Ketals" by John B. Brogan, Cary B. Bauer et al.
 

Study of the Rearrangements of Oxonium Ylides Generated from Ketals

Abstract

Intramolecular exposure of cyclic ketals to metal carbenoids generates a proposed oxonium ylide intermediate that subsequently rearranges to one of three general products. The product resulting from a 1,2-shift to the ketal carbon is favored by larger ketals that lack radical stabilizing groups. A bridged bicyclic structure is formed by competitive 1,2-shift to the exocyclic carbon of the ketal and is favored by smaller ketal ring sizes that possess radical-stabilizing groups. An alternative β-elimination pathway can also operate when neither of the 1,2-shift pathways are favored. The enol ether that is formed in this latter pathway rearranges easily to an isomeric dioxene.

Department

Chemistry

Publication Date

6-1-1997

Journal Title

Journal of Organic Chemistry

Publisher

American Chemical Society

Digital Object Identifier (DOI)

10.1021/jo961896m

Document Type

Article

Rights

Copyright © 1997 American Chemical Society

Link to Full Text

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