[Bis (diisopropylamino) phosphino] trimethylsilylcarbene: a stable nucleophilic carbene

A Igau, A Baceiredo, G Trinquier… - … International Edition in …, 1989 - Wiley Online Library
Angewandte Chemie International Edition in English, 1989Wiley Online Library
It is that up'-biscarbenes, generated from the corresponding bisdiazo derivatives 1 b, are
stable compounds; however, from their reactivity they must be regarded as alkynes rather
than as stable biscarbenes. The only argument for the carbene character of 2 was based on
the formation of the azaphospholidine 3 (carbene insertion into a carbon-hydrogen bond of
an isopropyl substituent) upon thermolysis of 2 at 300 oC.[zl The experimental conditions
used and the regioselectivity of the ring closure are consistent with this argument.
It is that up'-biscarbenes, generated from the corresponding bisdiazo derivatives 1 b, are stable compounds; however, from their reactivity they must be regarded as alkynes rather than as stable biscarbenes. The only argument for the carbene character of 2 was based on the formation of the azaphospholidine 3 (carbene insertion into a carbon-hydrogen bond of an isopropyl substituent) upon thermolysis of 2 at 300 oC.[zl The experimental conditions used and the regioselectivity of the ring closure are consistent with this argument.
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