228574-67-2Relevant articles and documents
Semipinacol Rearrangement Induced by Cleavage of Dibromocyclopropane
Kurimoto, Michitaka,Nakajima, Daisuke,Nishiyama, Yoshitake,Yokoshima, Satoshi
supporting information, p. 4108 - 4111 (2020/05/08)
A novel semipinacol rearrangement using dibromocyclopropanes as sources of carbocations was developed. Heating dibromocyclopropanes bearing a 1-hydroxyalkyl group with silver perchlorate and 2,6-lutidine induced cleavage of the cyclopropane ring to form allyl cations, which underwent 1,2-shift of a substituent at the α-position of the hydroxy group to give β,γ-unsaturated carbonyl compounds having a quaternary carbon at the α-position. Because the products have convertible functional groups such as bromo, vinyl, and formyl groups, the method is expected to be applicable to the synthesis of various molecules.
Rhodium promoted isomerisation of allylic alkoxides: A new method for enolate anion formation
Gazzard, Lewis J.,Motherwell, William B.,Sandham, David A.
, p. 979 - 993 (2007/10/03)
Transition metal mediated isomerisation of allylic alkoxides is presented as a new method for enolate anion generation. The scope and limitations of enolate formation with the catalysts [Rh(dppe)(THF)2]+ClO4- and (Ph3P)3RhCl are explored and the synthetic potential of the methodology demonstrated in the stereoselective formation and reactions of certain ketone and aldehyde enolates.
