Accession Number : ADA105433


Title :   Reactions of Tributylstannyl Anioniods with Alkyl Bromides.


Descriptive Note : Technical rept.,


Corporate Author : TEXAS A AND M UNIV COLLEGE STATION DEPT OF CHEMISTRY


Personal Author(s) : Newcomb,Martin ; Smith,Michael G


Full Text : https://apps.dtic.mil/dtic/tr/fulltext/u2/a105433.pdf


Report Date : 28 Sep 1981


Pagination or Media Count : 23


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)


Descriptors :   *HYDRIDES , *REACTION KINETICS , *BUTYL RADICALS , *TIN COMPOUNDS , SECONDARY , ORGANOMETALLIC COMPOUNDS , TRAPPING(CHARGED PARTICLES) , REPLACEMENT , ALKYLATION , FREE RADICALS , BROMIDES , ANIONS


Subject Categories : Organic Chemistry


Distribution Statement : APPROVED FOR PUBLIC RELEASE