ISSN:
0947-3440
Keywords:
Cinnamic acids
;
Cyclophanes
;
Topochemistry
;
Cycloadditions
;
Photochemistry
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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).
Additional Material:
4 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199719970215
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