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tris(2-Perfluorohexylethyl)tin azide: A new reagent for preparation of 5-substituted tetrazoles from nitriles with purification by fluorous/organic liquid-liquid extraction

Curran, DP and Hadida, S and Kim, SY (1999) tris(2-Perfluorohexylethyl)tin azide: A new reagent for preparation of 5-substituted tetrazoles from nitriles with purification by fluorous/organic liquid-liquid extraction. Tetrahedron, 55 (29). 8997 - 9006. ISSN 0040-4020

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Abstract

Summary: The synthesis of a new fluorous tin azide, (C6F13CH2CH2)3SnN3, is reported and this reagent is used to make tetrazoles in both traditional and phase-switching modes. In the traditional mode, the tin azide is reacted with nitriles followed by HCl cleavage to provide the tetrazoles and the fluorous tin chloride (which can be reconverted into the tin azide). In the switching mode, the initial tin tetrazole is purified by fluorous/organic liquid-liquid extraction prior to destannylation. This provides pure products even in incomplete reactions or with impure starting materials, but it only works for smaller nitriles.


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Details

Item Type: Article
Status: Published
Creators/Authors:
CreatorsEmailPitt UsernameORCID
Curran, DPcurran@pitt.eduCURRAN
Hadida, S
Kim, SY
Date: 16 July 1999
Date Type: Publication
Journal or Publication Title: Tetrahedron
Volume: 55
Number: 29
Page Range: 8997 - 9006
DOI or Unique Handle: 10.1016/s0040-4020(99)00458-5
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Refereed: Yes
ISSN: 0040-4020
Date Deposited: 26 Feb 2014 17:11
Last Modified: 05 Feb 2019 03:55
URI: http://d-scholarship.pitt.edu/id/eprint/20637

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