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Preparation of the Reagent o-Nitrobenzenesulfonylhydrazide

Myers, Andrew G. and Zheng, Bin and Movassaghi, Mohammad (1997) Preparation of the Reagent o-Nitrobenzenesulfonylhydrazide. Journal of Organic Chemistry, 62 (21). p. 7507. ISSN 0022-3263. https://resolver.caltech.edu/CaltechAUTHORS:20180720-154358162

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Abstract

o-Nitrobenzenesulfonylhydrazide (NBSH) has been shown to be a valuable reagent for the synthesis of allenes from propargylic alcohols, for the reductive transposition of allylic alcohols, and, most recently, for the deoxygenation of unhindered alcohols. Each of these transformations proceeds by Mitsunobu displacement of an alcohol with NBSH followed by in situ elimination of o-nitrobenzenesulfinic acid to form a monoalkyl diazene intermediate. The mild reaction conditions (neutral pH, reaction temperatures ≤23 °C) are especially attractive for substrates containing sensitive functional groups. The success of this methodology relies critically upon the purity of the NBSH reagent employed in the reaction. A simple and practical procedure for the preparation of NBSH of high purity and guidelines for the handling and storage of the reagent are provided in this note.


Item Type:Article
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https://dx.doi.org/10.1021/jo9710137DOIArticle
Additional Information:© 1997 American Chemical Society. Received June 6, 1997. This research was generously supported by the National Science Foundation.
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Issue or Number:21
Record Number:CaltechAUTHORS:20180720-154358162
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20180720-154358162
Official Citation:Preparation of the Reagent o-Nitrobenzenesulfonylhydrazide Andrew G. Myers, Bin Zheng, and Mohammad Movassaghi The Journal of Organic Chemistry 1997 62 (21), 7507-7507 DOI: 10.1021/jo9710137
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:88097
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:23 Jul 2018 21:26
Last Modified:03 Oct 2019 20:03

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