D.A.McL. Smith, S.A. Williams, et al.
Journal of Physical Chemistry
We describe here a simple synthesis of 2-(diazoacetyl)cyclobutanones and their facile thermal rearrangement to 5-spirocyclopropyl-Δα,β-butenolides. The yield of the rearrangement product is high, and the reaction is completely stereospecific. α-Ketenylcyclobutanones have been identified spectroscopically as intermediates, and their rearrangement was studied kinetically. A strained dipolar cyclic transition is proposed for the rearrangement of the α-ketenylcyclobutanones to the corresponding 5-spirocyclopropyl-Δα,β-butenolides. © 1991, American Chemical Society. All rights reserved.
D.A.McL. Smith, S.A. Williams, et al.
Journal of Physical Chemistry
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Molecular Crystals and Liquid Crystals Science and Technology Section B: Nonlinear Optics
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ACS Spring 1999
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