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Structure Investigation of Bridgehead Aziridine: Synthesis, Theoretical, and Crystallographic Study of 2,4,6-Triphenyl-1,3-diazabicyclo[3.1.0]hex-3-ene

✍ Scribed by Giuseppe Bruno; Francesco Nicolò; Archimede Rotondo; Francesco Risitano; Giovanni Grassi; Francesco Foti

Publisher
John Wiley and Sons
Year
2006
Tongue
German
Weight
313 KB
Volume
89
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

A one‐pot three‐component procedure to efficiently create the 1,3‐diazabicyclo[3.1.0]hex‐3‐ene system is reported. The molecular structure of 2,4,6‐triphenyl‐1,3‐diazabicyclo[3.1.0]hex‐3‐ene (3) was studied by X‐ray diffraction and compared to ab initio and density‐functional‐theory (DFT) calculations restricted to the core moiety. Geometry optimizations for structural isomers and tautomeric forms of this aziridine fragment, taken as simplified models, were carried out at high calculation levels. Moreover, the same methods were utilized to evaluate the proton affinity of two crucial aziridine tautomers.

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## Abstract 3,4‐Diazabicyclo[4.3.0]non‐2‐ene and __N,N'__‐azo‐3‐azabicyclo[3.3.0]octane are the main products of the oxidation of __N__‐amino‐3‐azabicyclo[3.3.0]octane by chloramine. These new compounds have been isolated and characterized. A structural study has been performed with the goal of est