Spontaneous conversion of O -tosylates of 2-(piperazin-1-yl)ethanols into chlorides during classical tosylation procedure | Zendy

Vanya B. Kurteva | Zendy; Boris Shivachev | Zendy; R. Petrova | Zendy

Open Access

Spontaneous conversion of O -tosylates of 2-(piperazin-1-yl)ethanols into chlorides during classical tosylation procedure

Author(s) -

Vanya B. Kurteva,

Boris Shivachev,

R. Petrova

Publication year - 2019

Publication title -

royal society open science

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.84

H-Index - 51

ISSN - 2054-5703

DOI - 10.1098/rsos.181840

Subject(s) - chemistry , algebra over a field , mathematics , pure mathematics

A direct conversion of piperazinyl ethanols into chlorides via a classical O -tosylation protocol is observed. The acceleration of the transformation by the piperazine unit is demonstrated. It is found that the reaction goes via the corresponding O -tosylate, which converts spontaneously into chloride with different rate depending on the substrate structure. In the case of pirlindole derivative, partially aromatized chloride formation was observed upon prolongation and/or increased excess of tosyl chloride.

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