Reactions of Tributylstannyl Anioniods with Alkyl Bromides.
Abstract
The reactions of tributylstannyl anionoids (Bu3SnM, M = Li, K, Cs) with alkyl bromides have been studied. Tributylstannylpotassium and -cesium were prepared by deprotonation of tributyltin hydride with the mixed deprotonating agents potassium (cesium) diisopropylamide/lithium tert-butoxide. The predominant mechanism for alkylation of tributylstannyl anionoids by primary bromides is an S(N)2 displacement or its mechanistic equivalent, but the reactions of tributylstannyllithium with two secondary bromides appear to involve free radicals as intermediates. Dicyclohexylphosphine, which serves as a trapping agent for intermediate free radicals, was found to react relatively slowly with tributylstannyllithium to give hexabutylditin. (Author)
Document Details
- Document Type
- Technical Report
- Publication Date
- Sep 28, 1981
- Accession Number
- ADA105433
Entities
People
- Martin Newcomb
- Michael G. Smith
Organizations
- Texas A&M University