119060-47-8Relevant articles and documents
Reactions of Organic Anions; CXLIX. Reactions of gem-Dichlorocyclopropanes Containing an Electron-Withdrawing Substituent with Organic Anions Generated with Phase-Transfer Catalysis
Fedorynski, Michal,Dybowska, Agnieszka,Jonczyk, Andrzej
, p. 549 - 551 (1988)
gem-Dichlorocyclopropanes 1 react with C-H, O-H and S-H acids in the presence of concentrated sodium hydroxide solution and a phase-transfer catalyst to give gem-disubstituted cyclopropanes 2 or chain products 3 in 44-95percent yield.
Catalyst Effects on Reactions of α,β-Unsaturated Ketones and Esters with Haloforms under Phase-Transfer Catalysis
Dehmlow, Eckehard V.,Wilkenloh, Juergen
, p. 582 - 588 (2007/10/02)
Reactions of acceptor-substituted alkenes with haloform/sodium hydroxide and PT-catalyst result in dihalocarbene additions competitive to Michael additions, with or without consecutive cyclization, and further reactions.Product compositions are strongly dependent on the nature of the phase-transfer catalyst: Sterically unhindered quarternary ammonium ions and benzo-crown ethers favour processes via carbenes, large delocalized (soft) cations foster primary Michael additions.Thus, tert-butyl cis-crotonate is dichlorocyclopropanated stereospecifically with NMe4Cl.The respective stereospecific CBr2 conversion is successful only with PhHgCBr3 .