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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| Format: | Article |
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Royal Society of Chemistry
1971
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| Online Access: | http://eprints.um.edu.my/24417/ https://doi.org/10.1039/J39710002275 |
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| Summary: | 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. |
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