Wiley InterScience Backfile Collection 1832-2000
Chemistry and Pharmacology
The pseudo-gem cinnamophane dicarboxylic acid 1 was shown to undergo a stereospecific [2 + 2] photocycloaddition in the solid state, generating the truxinic acid derivative 2 in 100% chemical yield; the reaction can proceed to completion because it is not an “independent site” solid state reaction. The X-ray structure of 1 reveals that its molecules are associated in dimers formed from four almost linear hydrogen bonds. A salient feature is the intramolecular centre-to-centre distance between the reacting double bonds of ≈3.37 Å, the smallest known to date. In contrast to trans-cinnamic acid, the topochemical [2 + 2] photocycloaddition occurs also in solution, with a quantitative chemical yield and a quantum yield of ≈0.55 (in methanol).
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