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

S.H. Goh

Document Type

Article

Publication Date

1-1-1971

Abstract

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.

Keywords

Nitrophenylcarbenes, catalytic, photolytic, decomposition, α-diazo-3-nitrotoluene, olefins

Divisions

CHEMISTRY

Publication Title

Journal of the Chemical Society C: Organic

Publisher

Royal Society of Chemistry

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