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Photochemical Reactions of Regioisomeric 2,2-Dimethyl-5,5-diphenyl- and 5,5-Dimethyl-2,2-diphenyl-Substituted Diazo Ketones of a Tetrahydrofuran Series by Ludmila L. Rodina; Sergey A. Malashikhin; Olesya S. Galkina; Valerij A. Nikolaev is a Chemistry article available to read on EtoBox.

What is Photochemical Reactions of Regioisomeric 2,2-Dimethyl-5,5-diphenyl- and 5,5-Dimethyl-2,2-diphenyl-Substituted Diazo Ketones of a Tetrahydrofuran Series about?

## Abstract The principal direction of conventional photolysis of the regioisomeric 2,2‐dimethyl‐5,5‐diphenyl‐ and 5,5‐dimethyl‐2,2‐diphenyl‐substituted 4‐diazodihydrofuran‐3(2__H__)‐ones **1a** and **1b**, respectively, is the __Wolff__ rearrangement, while other photochemical processes, which are giving rise to the formation of CH‐insertion, 1,2‐alkyl‐ or ‐aryl‐shifts, as well as H‐atom‐abstraction products occur to a much lower degree (__Schemes 2__ and __3__). The ratio of similar reaction products from both regioisomers **1a** and **1b** is essentially independent of their structure, and a substantial effect of the relative position of the Ph and diazo group to each other on the yield of CH‐insertion products does not occur. Based on stereochemical considerations, the __Wolff__ rearrangement of diazodihydrofuran‐3(2__H__)‐ones apparently proceeds in a concerted manner, whereas the appearance in the reaction mixture of 1,2‐shift and H‐atom‐abstraction products points to the parallel generation during photolysis of singlet and triplet carbenes (__Schemes 4__ and __5__).

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Author

Ludmila L. Rodina; Sergey A. Malashikhin; Olesya S. Galkina; Valerij A. Nikolaev

Publisher

John Wiley and Sons; Wiley (John Wiley & Sons); Wiley-Blackwell; Wiley (ISSN 0018-019X)

Published

2009

Language

EN

Field

Chemistry (Physical Sciences)