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Preparation, Structure, and Unique Thermal [2+2], [4+2], and [3+2] Cycloaddition Reactions of 4Vinylideneoxazolidin‐2‐one by Yoshikazu Horino; Masanari Kimura; Shuji Tanaka; Toshiya Okajima; Yoshinao Tamaru is a Chemistry article available to read on EtoBox.

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## Abstract The terminal allene C~__α__~C~__β__~ bonds of 4vinylidene‐2‐oxazolidinone (2) readily undergo [2+2] cycloaddition with a wide variety of terminal alkynes, alkenes, and 1,3‐dienes irrespective of their electronic nature under strictly thermal activation conditions (70–100 °C) and provide 3substituted (__Z__)‐methylenecyclobutenes 6, 3substituted methylenecyclobutanes 7 and 8, and 3vinylmethylenecyclobutanes 9, respectively, in good to excellent yields. Alkenes react with 2 with complete retention of configuration. The [2+2] cycloaddition is concluded to proceed via a concerted [(π~2s~+π~2s~)~allene~ + π~2s~] Hückel transition state on the basis of experimental evidences and quantum mechanical methods. Some highly polarized enones and nitrile oxide, on the other hand, react with 2 selectively at the internal C~4~C~__α__~ double bonds and give spiro compounds 10 and 11, respectively. The bent allene bonds (173–176°) and the unique reactivity associated with 2 are attributed to a low‐lying LUMO (C~__α__~C~__β__~) that is substantiated by a through‐space σ\*(N‐SO~2~)–π\*(C~__α__~C~__β__~) orbital interaction.

Who reads Preparation, Structure, and Unique Thermal [2+2], [4+2], and [3+2] Cycloaddition Reactions of 4Vinylideneoxazolidin‐2‐one?

Author

Yoshikazu Horino; Masanari Kimura; Shuji Tanaka; Toshiya Okajima; Yoshinao Tamaru

Publisher

John Wiley and Sons; Wiley (John Wiley & Sons); John Wiley & Sons Ltd.; Wiley (ISSN 0947-6539)

Published

2003

Language

EN

Field

Chemistry (Physical Sciences)