Chemistry Reference
In-Depth Information
12
PROPERTIES OF CARBONYL
NITRENES AND RELATED ACYL
NITRENES
N
INA
P. G
RITSAN
12.1 Introduction
12.2 Generation and Properties of Carbonyl Nitrenes
12.3 Generation and Properties of Nitrene Esters
12.4 Generation and Properties of Sulfonyl Nitrenes
12.5 Generation and Properties of Phosphinyl- and Phosphoryl Nitrenes
12.5.1 Phosphinyl Azides and Nitrenes
12.5.2 Phosphoryl Azides and Nitrenes
12.6 Conclusions
References
12.1
INTRODUCTION
Nitrenes are compounds containing neutral, monovalent nitrogen atoms, while most
stable compounds of neutral nitrogen have a valence of three. Thus, most nitrenes,
including acyl nitrenes, are very reactive and short-lived intermediates. It is a
commonly accepted view, presented in many reviews,
1-12
that the addition at double
bonds and the insertion into the C
H bonds are typical reactions
of singlet nitrenes. However, characteristic products of the bimolecular addition and
insertion reactions have been almost exclusively isolated for acyl nitrenes and
H, O
H, and N
