Kikumasa Sato, M. Hirayama
Sep 1, 1969
Citations
0
Influential Citations
1
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
The preparation of pent-2-en-4-ynylamine and pent-2-en-4-ynylthiol and their derivatives from 5-bromopent-3-en-1-yne was studied. Moreover, in connection with the preparation of the bromide, the rearrangement-bromination of vinylethynylcarbinol was found to give three isomeric bromides, 5-bromopent-trans-3-en-1-yne, 5-bromopent-cis-3-en-1-yne, and 3-bromopent-1-en-4-yne. Pent-2-en-4-ynylamine was obtained from 5-bromopent-3-en-1-yne by two methods, by the hydrolysis of the hexaminium salt and by the cleavage of N-(pent-2-en-4-ynyl)phthalimide. The reaction of 5-bromopent-3-en-1-yne with potassium hydrosulfide and the decomposition of ethyl pent-2-en-4-ynylxanthate by alcoholic ammonia gave pent-2-en-4-ynylthiol.