✍ Scribed by L. Wilputte-Steinert; L. P. A. Fery; J. Nasielski
No coin nor oath required. For personal study only.
Reaction of 2-methyl-2-benzyl-l,2,3,4-tetrahydroisoquinolinium iodide with sodium amide in liquid ammonia yields 76% l-orthotolyl-2-methy1-1,2,3,4-tetrahydroisoquinoline resulting from a Sommelet-Hauser rearrangement. In the same conditions, 2,2-dimethyl-1,2,3,4-tetrahydroisoquinolinium iodide yields 4% N,N-dimethyl-2-vinylbenzylamine resulting from an elimination reaction and 70% 1-(2-dimethylaminomethylphenyl)-2-[2-(~-dimethylaminoethylphenyl)]-cyclopropane, probably trans, (IX) resulting from dimerization followed by y-elimination.
📜 SIMILAR VOLUMES
## Abstract In order to examine the importance of Sommelet and Stevens rearrangement versus β‐elimination, the reaction of sodium amide in liquid ammonia on 1‐methyl‐benzylpiperidinium iodide was examined and found to give three isomeric tertiary bases: two of them resulting from a Sommelet rearran
The reaction of sodium amide in liquid ammonia on l-methyl-l-benzylpyrrolidinium iodide was examined and found to give two isomeric tertiary bases: one of them (yield 86%) results from a Sommelet rearrangement, the other (yield 5%) is formed through a Stevens rearrangement. Dans un article priceden