ISSN:
0009-2940
Keywords:
Rule of five
;
[2 + 2] Photocycloaddition
;
Regiochemistry
;
Enones
;
Vinyl ethers
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The intramolecular [2 + 2] cycloaddition of a cyclohexenone moiety bound to a vinyl ether fragment has been explored. The regiochemistry and the quantum yield of the reaction have been investigated as a function of the chain length n and the position of the methoxy group. It has been found that in those cases where the chain consists of three and four members the position of the methoxy group has no influence on the regiochemistry but on the quantum yield. Only head-to-head cycloaddition is observed. In the case of n = 2 both the regiochemistry and the quantum yield depend strongly on the position of the methoxy group. It is concluded that the main reason for the different behavior of n = 2 is due to a through-bond effect between the two olefinic units mediated by a C2H4 bridge.
Additional Material:
3 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19921250818
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