38846-06-9Relevant academic research and scientific papers
Deamination of 3-(dialkylamino)-1,4-diarylhex-5-en-1-ynes during vacuum distillation
Chukhajian,Shahkhatuni,Chukhajian, El. O.,Ayrapetyan,Panosyan
, p. 178 - 183 (2017/04/21)
During vacuum distillation of 3-(dialkylamino) derivatives of 1,4-diphenyl- and 4-phenyl-1-(p-chlorophenyl) hex-5-en-1-ynes deamination occurs resulting in a high yield of p-diarylbenzenes. The amines transformation into terbenzenes is a domino-reaction: first step consists in the β-elimination of secondary amines with the generation of conjugated dienyne which via an electrocyclic reaction transforms into cyclic allene intermediate. The latter after 1,3- or 1,5-hydride shift quickly converts into the final reaction products.
Base Catalysed Rearrangements involving Ylide Intermediates. Part 1. The Rearrangements of Diallyl- and Allylpropynyl-ammonium Cations
Jemison, Robert W.,Laird, Trevor,Ollis, W. David,Sutherland, Ian O.
, p. 1436 - 1449 (2007/10/02)
The base catalysed rearrangements of diallylammonium cations and allylpropynylammonium cations are described.In most cases, the major product arises by a symmetry-allowed sigmatropic rearrangement of the intermediate ylide.The minor products can be regarded as being derived by homolysis of the ylide into a radical pair followed by recombination.
Base Catalysed Rearrangements involving Ylide Intermediates. Part 6. The Rearrangements of Diallyl- and Allylpropynyl-ammonium Cations in Protic Media
Laird, Trevor,Ollis, W. David,Sutherland, Ian O.
, p. 1477 - 1486 (2007/10/02)
The base catalysed rearrangements of the cations (1d-j) in aqueous solution yield the isomeric cations (15) or the aldehydes (10) and (11), or mixtures of (15), (10), and (11).This contrasts dramatically with the transformations observed for the cations (1) in aprotic solvents.The cations (15) undergo Hofmann elimination to the naphthalenic amines (12) or (13) and (14).The methiodide of amine (13g) shows a novel consequence of restricted rotation.The n.m.r. spectrum of the methiodide shows that the two protons of the methylene group are diastereotopic.
Base-catalysed rearrangement of allyl-propynyl ammonium cations and a novel synthetic route to substituted biphenyls
Jemison,Laird,Ollis
, p. 556 - 557 (2007/10/06)
Base-catalysed rearrangement of the salts (I) in aprotic media gives the amines (II) and (III); the amines (II) on heating yield the biphenyl derivatives (V).
