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Matrix Isolation of o ‐Quinoid Compounds – 6‐Imino‐2,4‐cyclohexadien‐1‐one and 1,2‐Diimino‐3,5‐cyclohexadiene by Jens Morawietz; Wolfram Sander is a Chemistry article available to read on EtoBox.

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## Abstract 6‐Imino‐2,4‐cyclohexadien‐1‐one (1b) and 1,2‐diimino‐3,5‐cyclohexadiene (1c) were generated in high yields from __o__‐azidophenol (5b) and __o__‐azidoaniline (5c), respectively, by irradiation in argon matrices at 10 K or by flash vacuum pyrolysis (FVP) with subsequent trapping of the products in solid argon. The hydrogen shift in the phenylnitrenes 6 formed as primary intermediates is very rapid, and thus the nitrenes are short‐lived transients even under the conditions of matrix isolation. Ring expansion to azacycloheptatetraenes was not observed. FVP produces the thermodynamically most stable __E/Z__ isomers of the quinones as the main products. Photolysis of the matrix‐isolated quinones results in photostationary equilibria of the __E/Z__ isomers. The stereoisomers were identified by comparison of the matrix IR spectra with ab initio calculations at the RMP2‐FC‐6/31G(d) level of theory.

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Author

Jens Morawietz; Wolfram Sander

Publisher

John Wiley and Sons; Wiley (John Wiley & Sons); VCH Verlagsgesellschaft; Wiley (ISSN 0947-3440)

Published

1996

Language

DE

Field

Chemistry (Physical Sciences)