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Issue 12, 2012
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Solid-state photochemistry of crystalline pyrazolines: reliable generation and reactivity control of 1,3-biradicals and their potential for the green chemistry synthesis of substituted cyclopropanes

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Abstract

To expand on the limited number of examples that exist in the literature for the solid-state photodenitrogenation of azoalkanes, a series of crystalline 7-alkyl-2,3,7-triazabicyclo[3.3.0]oct-2-ene-6,8-diones with varying 4,4-substituents were prepared. Their photochemical behavior in solution and in the solid state was dependent on the 4,4-substitution of the 1-pyrazoline ring, with unsubstituted pyrazoline 12 giving a mixture of products both in solution and in the solid state. Diphenyl substituted pyrazolines 13 denitrogenate spontaneously in solution but require light exposure to react quantitatively in the solid state. t-Butyl-phenyl substituted pyrazolines 14 were shown to denitrogenate both chemo- and diastereoselectively in solution and in the solid state to yield a single product in quantitative yield.

Graphical abstract: Solid-state photochemistry of crystalline pyrazolines: reliable generation and reactivity control of 1,3-biradicals and their potential for the green chemistry synthesis of substituted cyclopropanes

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Article information


Submitted
24 Jul 2012
Accepted
16 Aug 2012
First published
16 Aug 2012

Photochem. Photobiol. Sci., 2012,11, 1929-1937
Article type
Paper

Solid-state photochemistry of crystalline pyrazolines: reliable generation and reactivity control of 1,3-biradicals and their potential for the green chemistry synthesis of substituted cyclopropanes

S. Shiraki, C. S. Vogelsberg and M. A. Garcia-Garibay, Photochem. Photobiol. Sci., 2012, 11, 1929 DOI: 10.1039/C2PP25263E

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