ISSN:
1573-9171
Keywords:
crown ether styryl dyes
;
synthesis
;
complexation
;
anion-“capped” complexes
;
[2+2] photocycloaddition
;
cyclobutane derivatives
;
1H NMR spectra
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Abstract New crown ether styryl dyes (trans-1c,d) containing the 18-crown-6 ether fragment were synthesized. Interaction oftrans-1c,d dyes, as well as their analogs,trans-1a,b containing the 15-crown-5 ether fragment, with Ca(ClO4)2 in MeCN afforded supramolecular structures (dimeric complexes). Competing reactions,trans-cis-photoisomerization with the formation of anion-“capped” complexes ofcis-1a—d and [2+2] autophotocycloaddition with the formation of cyclobutane derivatives8a—d and9c, were observed on photolysis of solutions of complexes oftrans-1a—d with Ca2+. Preorganization oftrans-isomers in dimeric complexes with Ca2+ determined the regio- and stereoselectivity of each of the two directions of the photocycloaddition and the efficiency of the reaction.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF01435800
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