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Nitrophenylcarbenes. Part I. The catalytic and photolytic decomposition of α-diazo-3-nitrotoluene in the presence of olefins

The decomposition of α-diazo-3-nitrotoluene by zinc halides in the presence of olefins gave cyclopropane adducts in moderate yields. The addition of the carbenoid intermediate to unsymmetrically substituted olefins is syn-stereoselective. The free carbene species generated by photolysis also added r...

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Main Author: Goh, S.H.
Format: Article
Published: Royal Society of Chemistry 1971
Subjects:
Q Science (General)
QD Chemistry
Online Access:http://eprints.um.edu.my/24417/
https://doi.org/10.1039/J39710002275
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spelling my.um.eprints.244172021-03-24T05:28:53Z http://eprints.um.edu.my/24417/ Nitrophenylcarbenes. Part I. The catalytic and photolytic decomposition of α-diazo-3-nitrotoluene in the presence of olefins Goh, S.H. Q Science (General) QD Chemistry The decomposition of α-diazo-3-nitrotoluene by zinc halides in the presence of olefins gave cyclopropane adducts in moderate yields. The addition of the carbenoid intermediate to unsymmetrically substituted olefins is syn-stereoselective. The free carbene species generated by photolysis also added readily to olefins. Non-stereospecific cyclopropane adducts and olefinic products were also formed, as a result of the involvement of both singlet and triplet 3-nitrophenylcarbenes. Royal Society of Chemistry 1971 Article PeerReviewed Goh, S.H. (1971) Nitrophenylcarbenes. Part I. The catalytic and photolytic decomposition of α-diazo-3-nitrotoluene in the presence of olefins. Journal of the Chemical Society C: Organic. pp. 2275-2278. ISSN 0022-4952 https://doi.org/10.1039/J39710002275 doi:10.1039/J39710002275
institution Universiti Malaya
building UM Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Malaya
content_source UM Research Repository
url_provider http://eprints.um.edu.my/
topic Q Science (General)
QD Chemistry
spellingShingle Q Science (General)
QD Chemistry
Goh, S.H.
Nitrophenylcarbenes. Part I. The catalytic and photolytic decomposition of α-diazo-3-nitrotoluene in the presence of olefins
description The decomposition of α-diazo-3-nitrotoluene by zinc halides in the presence of olefins gave cyclopropane adducts in moderate yields. The addition of the carbenoid intermediate to unsymmetrically substituted olefins is syn-stereoselective. The free carbene species generated by photolysis also added readily to olefins. Non-stereospecific cyclopropane adducts and olefinic products were also formed, as a result of the involvement of both singlet and triplet 3-nitrophenylcarbenes.
format Article
author Goh, S.H.
author_facet Goh, S.H.
author_sort Goh, S.H.
title Nitrophenylcarbenes. Part I. The catalytic and photolytic decomposition of α-diazo-3-nitrotoluene in the presence of olefins
title_short Nitrophenylcarbenes. Part I. The catalytic and photolytic decomposition of α-diazo-3-nitrotoluene in the presence of olefins
title_full Nitrophenylcarbenes. Part I. The catalytic and photolytic decomposition of α-diazo-3-nitrotoluene in the presence of olefins
title_fullStr Nitrophenylcarbenes. Part I. The catalytic and photolytic decomposition of α-diazo-3-nitrotoluene in the presence of olefins
title_full_unstemmed Nitrophenylcarbenes. Part I. The catalytic and photolytic decomposition of α-diazo-3-nitrotoluene in the presence of olefins
title_sort nitrophenylcarbenes. part i. the catalytic and photolytic decomposition of α-diazo-3-nitrotoluene in the presence of olefins
publisher Royal Society of Chemistry
publishDate 1971
url http://eprints.um.edu.my/24417/
https://doi.org/10.1039/J39710002275
_version_ 1696976583864090624
score 13.19449

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