Reaction of N-phenyltriflamide with 1,2-dibromoethane and propargyl bromide. Unexpected cleavage of С–С and С–N bonds
- 作者: Shainyan B.A.1, Danilevich Y.S.1
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隶属关系:
- Favorskii Irkutsk Institute of Chemistry, Siberian Branch
- 期: 卷 52, 编号 8 (2016)
- 页面: 1112-1117
- 栏目: Article
- URL: https://journals.rcsi.science/1070-4280/article/view/214799
- DOI: https://doi.org/10.1134/S1070428016080030
- ID: 214799
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详细
Reaction of N-phenyltriflamide with 1,2-dibromoethane under basic conditions in DMSO unexpectedly results in N-methyl-N-phenyltriflamide and 1,3-diphenylurea. The presumed reaction mechanism includes the formation of unstable intermediate disubstitution product TfN(Ph)CH2CH2N(Ph)Tf that suffers the the С–С bond cleavage resulting in TfN(Me)Ph and N,N′-methanediylbis(N-phenyltriflamide). The latter reacts with K2CO3 releasing two molecules of potassium triflinate and after hydrolysis of diphenylcarbodiimide PhN=C=NPh gives 1,3-diphenylurea. With propargyl bromide, N-phenyltriflamide affords N-propargyl-Nphenyltriflamide in high yield. The bromination of the latter results in a mixture of Z,E-isomers of N-(2,3-dibromoprop-2-en-1-yl)-N-phenyltriflamide which undergo dehydrobromination giving first N-(3-bromopropanedienyl)-N-phenyltriflamide and then the products of the C–N bond cleavage: N-phenyltriflamide and 3,3-dimethoxyprop-1-yne.
作者简介
B. Shainyan
Favorskii Irkutsk Institute of Chemistry, Siberian Branch
编辑信件的主要联系方式.
Email: bagrat@irioch.irk.ru
俄罗斯联邦, ul. Favorskogo 1, Irkutsk, 664033
Yu. Danilevich
Favorskii Irkutsk Institute of Chemistry, Siberian Branch
Email: bagrat@irioch.irk.ru
俄罗斯联邦, ul. Favorskogo 1, Irkutsk, 664033
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