Solid-state photochromism and photoreactivity of o- and p-anisaldehydes. Remarkable stabilization of o-Xylylenols

Narasimha Moorthy, J. ; Mal, Prasenjit ; Natarajan, R. ; Venugopalan, P. (2001) Solid-state photochromism and photoreactivity of o- and p-anisaldehydes. Remarkable stabilization of o-Xylylenols Organic Letters, 3 (10). pp. 1579-1582. ISSN 1523-7060

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Official URL: http://pubs.acs.org/doi/abs/10.1021/ol0158720

Related URL: http://dx.doi.org/10.1021/ol0158720

Abstract

All of the crystalline o-anisaldehyde derivatives 1 and 3 change to brick-red color upon brief exposure to UV-vis radiation. The red color, attributed to (E)-xylylenol, is remarkably persistent for hours (ca. 10 h) in the case of 1c; such a long lifetime for the reactive o-xylylenols is unprecedented. In contrast, the p-anisaldehydes 2 undergo cyclization. Solid-state photolysis of 2b affords the benzocyclobutenol 7b regioselectively, which is not accessible from solution-phase photolysis.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:60760
Deposited On:10 Sep 2011 11:33
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