79840-73-6Relevant academic research and scientific papers
Tandem catalytic allylic amination and [2,3]-stevens rearrangement of tertiary amines
Soheili, Arash,Tambar, Uttam K.
, p. 12956 - 12959 (2011/10/08)
We have developed a catalytic allylic amination involving tertiary aminoesters and allylcarbonates, which is the first example of the use of tertiary amines as intermolecular nucleophiles in metal-catalyzed allylic substitution chemistry. This process is
Amines and ammonium salts: CCXXXVI. Stevens rearrangement of ammonium salts containins a 3,3-dimethylbutanoylmethyl and an allyl groups
Kocharyan,Karapetyan,Churkina
, p. 1098 - 1100 (2007/10/03)
Ammonium salts with a 3,3-dimethylbutanoylmethyl and an allyl groups undergo either 3,2 or simultaneously 3,2 and 1,2 Stevens rearrangements, depending on the γ-substituent in the migrating group. On heating, 3,2-rearrangement products isomerize into 1,2-rearrangement products.
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.
