Deamination Reactions, 45. Decomposition of 1-Arylcyclopropanediazonium Ions
1-Arylcyclopropanediazonium ions have been generated by alkaline cleavage of the analogous nitrosocarbamates in methanol.With increasing ?-donor capacity of the aryl groups, retention of the three-membered ring was enhanced while the stereoselectivity (as probed with the aid of 2-D labels) was diminished or entirely lost (4-methoxyphenyl).Where applicable, the stereoselectivity of ring opening is inferior to that of nucleophilic displacement.The data may be interpreted in terms of competing reactions (ks, kc, kΔ) of the cyclopropanediazonium ions.
Kirmse, Wolfgang,Rode, Jutta
p. 3694 - 3703
(2007/10/02)
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