Ethyl and tert-Butyl N-(4-nitrobenzenesulfonoxy)carbamates

The title compounds have been known for many years and have been widely used to generate alkoxycarbonylnitrenes by α-elimination as well as for other synthetic transformations. Although they have previously been characterised by spectroscopic methods, their X-ray structures are reported here for the first time. They have similar folded molecular structures but, while the ethyl ester forms hydrogen-bonded ribbons consisting of two rows of molecules joined by carbamate N–H⋯O=C hydrogen bonding, the tert-butyl ester forms hydrogen-bonded dimers involving the carbamate N–H and one sulfonyl O=S.

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Publication Details

Journal
Molbank
Published
2026-11-04
DOI
https://doi.org/10.3390/m2251
Primary Topic
Crystal structures of chemical compounds
Type
article
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article

Ethyl and tert-Butyl N-(4-nitrobenzenesulfonoxy)carbamates

David B. Cordes, R. A. Aitken, Edouard Famel
Molbank
Crystal structures of chemical compounds
article

Ethyl and tert-Butyl N-(4-nitrobenzenesulfonoxy)carbamates

David B. Cordes, R. A. Aitken, Edouard Famel
article en

Abstract

The title compounds have been known for many years and have been widely used to generate alkoxycarbonylnitrenes by α-elimination as well as for other synthetic transformations. Although they have previously been characterised by spectroscopic methods, their X-ray structures are reported here for the first time. They have similar folded molecular structures but, while the ethyl ester forms hydrogen-bonded ribbons consisting of two rows of molecules joined by carbamate N–H⋯O=C hydrogen bonding, the tert-butyl ester forms hydrogen-bonded dimers involving the carbamate N–H and one sulfonyl O=S.

MolbankVol. 2026(6)
University of St Andrews (GB)
Openalex Percentile: Top 29%
Crystal structures of chemical compounds
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