ISSN:
0009-2940
Keywords:
Photoinduced electron transfer
;
Cyclization
;
Ring opening
;
Enones
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Photolysis of the unsaturated enones 1 yields [2 + 2] cycloaddition products 2 and 3 with varying regioselectivity. Under electron-transfer conditions (PET) spirocyclic products 4 are formed. The straight [2 + 2] cycloaddition products 2b,c,f are converted to the spirocyclic products 4b,c,f under the same reaction conditions. The cyclobutane 5 and the cyclopropane 11 also undergo this new reductive ring opening reaction, while the stabilized system 7 is converted to reduced ringenlarged triquinane 10 which may be interesting in natural product synthesis. - Irradiation of 2-cyclohexen-1-one (14) in the presence of N,N-dimethylallylamine (15) leads to the decahydroisoquinoline 18. A mechanism involving radical intermediates is discussed.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19921250921
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