ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The Photochemistry of Conjugated Epoxy-enones: Photolysis of 9-Isopropyl-6-methyl-9,10-epoxybicyclo [4.4.0]dec-l-en-3-onThe title compound 1 undergoes on π, π*-excitation vinylogous β-cleavage of the C(γ), O-bond and isomerizes to the unsaturated 1, 5-diketone8(58%) and the tricyclic diketone9 (14%). On n, π*-excitation, however, 1 undergoes only desoxygenation to the dienone 7 (ca. 15%) besides polymerization. UV.-irradiation of 1 (λ ≥ 347 nm) in the presence of tributyl-stannane gives 7 in 85% yield; in the presence of tributylstannane-d1 1 yields 13, the deuterated analogon of 7 (85% yield; d1 ca. 50%); 7 has been proven to be stable on π, π* - as well as on n, π*-excitation.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19780610209