COMPETITIVE REARRANGEMENTS. I. NEOPENTYLIC VERSUS SKELETAL BICYCLOOCTANE -> BICYCLOOCTANE REARRANGEMENTS
Generation of a carbenium ion common to two systems which are able to undergo either a skeletal bicyclooctane --> bicyclooctane rearrangement or a neopentylic rearrangement conducts only to the latter reaction. Thus, 8-carbomethoxy-7-t-butyl-dibenzobicyclooctatriene (15) reacts with strong acids or bromine, yielding neopentyl rearranged products 17, respectively 21. Reaction mechanisms are proposed.
Ionica, Ileana,Ghiviriga, Ion,Filip, Petru,Badea, Florin,Dinulescu, Ilie G.
p. 1007 - 1016
(2007/10/03)
A CONVENIENT ROUTE TO ALKYNES VIA PHASE TRANSFER CATALYSIS; ( APPLICATIONS OF PHASE TRANSFER CATALYSIS, PART 19 )
High yield, rapid formations of alkynes from vic-dibromides are possible using powered potassium hydroxide and catalytic amounts of lipophilic phase transfer catalysts.Reasons are given why molar amounts of expensive catalysts were necessary in earlier procedures.
Dehmlow, Eckehard V.,Lissel, Manfred
p. 1653 - 1658
(2007/10/02)
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