Solid-state diphotocyclization of iso- and terephthalaldehydes via dihalogen substitution

Narasimha Moorthy, J. ; Venkatakrishnan, P. ; Mal, Prasenjit ; Venugopalan, P. (2003) Solid-state diphotocyclization of iso- and terephthalaldehydes via dihalogen substitution Journal of Organic Chemistry, 68 (2). pp. 327-330. ISSN 0022-3263

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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo026055w

Related URL: http://dx.doi.org/10.1021/jo026055w

Abstract

The supramolecular nonbonded C-H···X interactions between formyl hydrogens and ortho-halogen atoms (Br/Cl) have been exploited to achieve conformational control in the solid state of dimethyl-substituted iso- and terephthaladehydes (1-3) for unprecedented diphotocyclization. It is shown that the dihalogen substitution also contributes to the stability of the benzocyclobutenols relative to their precursor photoenols, so that the solid-state photolysis of dialdehydes 2b, 2c, and 3b leads to diphotocyclization to afford respectable yields of bis-benzocyclobutenols.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:60761
Deposited On:10 Sep 2011 11:37
Last Modified:10 Sep 2011 11:37

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