75376-88-4Relevant 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.
Cyclization of dialkyl(3-phenylpropen-2-yl)-(3-phenylpropyn-2-l)ammonium bromides by the action of an aqueous alkali solution. aqueous-alkaline cleavage of the cyclization products - N,n-dialkyl-4(9)-phenyl-3a,4-dihydro-benzo[f] isoindolinium bromides
Chukhajian,Ayrapetyan,Chukhajian, El. O.,Panosyan
, p. 1314 - 1320 (2013/04/24)
When heated in an alkaline aqueous medium, dialkyl(3-phenylpropen-2-yl)(3- phenylpropyn-2-yl)- ammonium bromides undergo intramolecular cyclization, forming N,N-dialkyl-4(9)-phenyl-3a,4-dihydrobenzo[f]isoindolinium bromides. The cyclization products undergo aqueous-alkaline cleavage at the C(1)-N(2) or N(2)-C(3) bond, which leads to a mixture of 2-(dialkylaminomethyl)-3-methyl- and 3-(dialkylaminomethyl)-2-methyl-1-phenylnaphthalenes. However, only the C(1)-N(2) bond cleavage product is formed in the case of 2,2-pentamethylene-9- phenyl-3a,4-dihydrobenzo-[f]isoindolinium bromide.
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 in protic media
Laird,Ollis
, p. 557 - 559 (2007/10/05)
The base-catalysed rearrangement of the allylpropynyl ammonium cations (I) in aqueous solution yields either the isomeric cations (II) or the aldehydes (III) and (IV), or mixtures of (II), (III), and (IV); this result contrasts dramatically with the trans
