244056-15-3Relevant articles and documents
Neighbouring-group influence on the ring opening of 2-aryloxymethyl-1,1,2-tribromocyclopropanes under phase-transfer conditions
Bakstad, Einar,Olsen, Are S.,Sandberg, Marcel,Sydnes, Leiv K.
, p. 465 - 472 (2007/10/03)
When a number of 2-aryloxymethyl-1,1,2-tribromocyclopropanes were treated with sodium hydroxide and ethanol under phase-transfer conditions, ring opening occurred to give mixtures of acetylenic diethyl acetals and ketals in better than 80% total isolated yield. The acetylenic diethyl ketals predominated significantly and were, in some cases, almost the exclusive product. It is argued that this ketal selectivity is in part caused by hydrogen bonding between ethanol and the aryloxy group.