29707-60-6Relevant academic research and scientific papers
A convenient and mild chromatography-free method for the purification of the products of Wittig and Appel reactions
Byrne, Peter A.,Rajendran, Kamalraj V.,Muldoon, Jimmy,Gilheany, Declan G.
supporting information; experimental part, p. 3531 - 3537 (2012/05/20)
A mild method for the facile removal of phosphine oxide from the crude products of Wittig and Appel reactions is described. Work-up with oxalyl chloride to generate insoluble chlorophosphonium salt (CPS) yields phosphorus-free products for a wide variety of these reactions. The CPS product can be further converted into phosphine.
Fragmentation of menthyl- and neomenthyloxychlorocarbenes: Elimination and substitution reactions of alicyclic oxychlorocarbenes
Moss, Robert A.,Johnson, Lauren A.,Kacprzynski, Monica,Sauers, Ronald R.
, p. 5114 - 5118 (2007/10/03)
Fragmentations of menthyloxychlorocarbene (5) and neomenthyloxychlorocarbene (6) follow distinct pathways to (largely) stereochemically retained substitution products from 5 and elimination products from 6, closely resembling the product distributions from deaminations of the corresponding menthyl- and neomenthylamines.
Reactions of Cyclohexane Derivatives in Superacids
Dean, Christopher,Whittaker, David
, p. 1541 - 1543 (2007/10/02)
The reactions of menthol with FSO3H-SO2 and neomenthyl chloride with SbF5-SO2ClF follow different routes.The first yields a substituted cyclopentyl cation and the second a substituted cyclohexyl cation.Experiments on substituted cyclohexyl chlorides show that replacement of all the hydrogen atoms on the next but one carbon atom to the reaction centre blocks formation of a carbocation.It is suggested that ionisation of an equatorial chlorine atom takes place with assistance from an intramolecular electronic interaction, forming the methyl cyclopentyl carbocation in a synchronous process, rather than stepwise via the cyclohexyl carbocation.Reasons for contrasting behaviour in solvolytic reactions are discussed.
Models for the Ion-Pair Cluster Mechanism in Nucleophilic Substitution Reactions
Ramos, Socorro,Rosen, William
, p. 3530 - 3533 (2007/10/02)
Several bis(alkoxytriphenylphosphonium) salts have been prepared.When sterically constrained, as close neighbors, the leaving groups of these cations react rapidly at room temperature with negative nucleophiles to produce the expected substitution product.When sterically unconstrained, these types of functional groups behave as if they were mono(alkoxytriphenylphosphonium) salts, substituting very slowly or not at all at room temperature.The ion-pair cluster mechanism is discussed in light of these results.
