The Formation of Tin-Nitrogen Bonds. V. The Selective 1-Substitution Reaction of Tetrazoles by the Reaction of 5-Substituted 2-(Tri-n-butylstannyl)tetrazoles with Methyl Iodide, Methylp-Toluenesulfonate, Dimethyl Sulfate, and Ethyl Bromoacetate | Zendy

Tyûzô Isida | Zendy; Tetsuo Akiyama | Zendy; Kiyoshi Nabika | Zendy; Keiiti Sisido | Zendy; Sinpei Kozima | Zendy

Open Access

The Formation of Tin-Nitrogen Bonds. V. The Selective 1-Substitution Reaction of Tetrazoles by the Reaction of 5-Substituted 2-(Tri-n-butylstannyl)tetrazoles with Methyl Iodide, Methylp-Toluenesulfonate, Dimethyl Sulfate, and Ethyl Bromoacetate

Author(s) -

Tyûzô Isida,

Tetsuo Akiyama,

Kiyoshi Nabika,

Keiiti Sisido,

Sinpei Kozima

Publication year - 1973

Publication title -

bulletin of the chemical society of japan

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.145

H-Index - 99

eISSN - 1348-0634

pISSN - 0009-2673

DOI - 10.1246/bcsj.46.2176

Subject(s) - chemistry , methyl iodide , tin , substitution reaction , substitution (logic) , nitrogen , iodide , medicinal chemistry , organic chemistry , computer science , programming language

The selective 1-substitution reaction of tetrazole was developed by the treatment of 5-substituted 2-(tri-n-butylstannyl)tetrazoles with methyl iodide, methyl p-toluenesulfonate, dimethyl sulfate, or ethyl bromoacetate at room temperature. This selectivity was introduced by blocking the 2-nitrogen with the tri-n-butyltin group against the 2-substitution. In the case of 5-substituted 2-(trimethylstannyl)tetrazoles, a low selectivity was observed. The possible reaction pathways have been discussed.

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