95317-45-6Relevant academic research and scientific papers
Base Catalysed Rearrangements Involving Ylide Intermediates. Part 9. The Rearrangement Reactions of Cyclic Allylic Ammonium and Sulphonium Ylides
Mageswaran, Sivapathasuntharam,Ollis, W. David,Sutherland, Ian O.
, p. 1953 - 1962 (2007/10/02)
The allylic ammonium ylides (22) and (47) and sulphonium ylide (53) are isolable, usually as crystalline solids, because their sigmatropic rearrangements are inhibited by the strain associated with the bicyclic transition state of a concerted reaction mechanism.The tetrahydropyridinium (22) and dihydrothiopyranium (29) ylides undergo a thermal rearrangement, but the pyrrolinium ylide (47) rearranges by a , rather than a , sigmatropic pathway.The dihydrothiophenium ylide (53) does not undergo either a or sigmatropic rearrangement but instead reacts in a bimolecular fashion to give eventually buta-1,3-diene, 2,5-dihydrothiophen, and the heterocycle (55).The rearrangements of the ylides (22) and (29) follow predominantly an endo-pathway leading to a single diastereomer of the products (23) and (31); this strong endo preference is not shown by analogous acyclic ammonium ylides.
Base Catalysed Rearrangements involving Ylide Intermediates. Part 2. The Stevens and Sigmatropyc Rearrangements of Allylic Ammonium Ylides
Jemison, Robert W.,Laird, Trevor,Ollis, W. David,Sutherland, Ian O.
, p. 1450 - 1457 (2007/10/02)
The base catalysed rearrangements of the quaternary ammonium salts (9) usually gives the sigmatropic rearrangement product (10) rather than the Stevens rearrangement product (11).An earlier claim has been corrected: the corresponding reaction
