D. Seyferth, M. Eisert, J. K. Heeren
Jul 1, 1964
Citations
0
Influential Citations
16
Citations
Journal
Journal of Organometallic Chemistry
Abstract
Abstract Methyllithium attacks tert -butyltriphenylphosphonium bromide principally at the phosphorus atom, giving benzene (68%) and tert -butyldiphenylphosphinemethylene (46% as methylenecyclohexane after its reaction with cyclohexanone). Ethyllithium shows reaction in this sense to a lesser degree, giving benzene and tert -butyldiphenylphosphineethylidene in yields of 30% and 25% respectively. With lithium piperidide formation of 9-phenyl-9-phosphafluorene in 42.4% yield was found; some 16% β -elimination also was observed in this reaction. Thus in the RLi ÷ [(C 6 H 5 ) 3 PC(CH 3 ) 3 ]Br reactions electronic factors appear to be more important than steric factors.