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Issue 3, 1989
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Imines and derivatives. Part 22. Photoisomerization of the N,N′-dioxides of N,N′-dialkyl-2,2,4,4-tetramethylcyclobutane-1,3-di-imines

Abstract

Photoisomerization of the N,N′-dioxides of two N,N′-dialkyl-2,2,4,4-tetramethylcyclobutane-1,3-di-imines occurs in a stepwise manner via the analogous mono-oxaziridine-mononitrone, dioxaziridine (and/or monoamide-mononitrone), and monoamide-mono-oxaziridine intermediates en route to the diamide products. The relative configurations of all products have been deduced by n.m.r. methods (chemical shift non-equivalence and n.O.e.d. spectroscopy). The stereochemistry of the photoisomerization reactions can be rationalized in terms of steric and stereoelectronic effects.

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Article type: Paper
DOI: 10.1039/P19890000537
J. Chem. Soc., Perkin Trans. 1, 1989, 537-541

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    Imines and derivatives. Part 22. Photoisomerization of the N,N′-dioxides of N,N′-dialkyl-2,2,4,4-tetramethylcyclobutane-1,3-di-imines

    A. J. Boyd, D. R. Boyd, N. D. Sharma, K. Dev, W. B. Jennings and O. W. Howarth, J. Chem. Soc., Perkin Trans. 1, 1989, 537
    DOI: 10.1039/P19890000537

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