ISSN:
0009-2940
Keywords:
Epoxidation
;
Dioxirane, dimethyl-
;
Benzofurans, 2,3-dimethyl-
;
Benzofuran epoxides
;
Quinone methides
;
[2 + 2] Photocycloaddition
;
Benzoxetes
;
Hetero-Diels-Alder reaction
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Irradiation (λ 〉 366 nm) of the quinone methides 3, which were formed by valence isomerization of the methyl-, chloro-, and tert-butyl-substituted 2,3-dimethylbenzofuran epoxides 2, afforded the novel 2H-benzoxetes 4 by photochemical [2 + 2] cycloaddition. These strained and highly labile benzoxetes 4 were spectrally (1H and 13C NMR) characterized at subambient temperatures. On prolonged storage (2-3 d) at -20 to -10°C, the benzoxetes 4 reverted to the quinone methides 3 and/or benzofuran epoxides 2.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19941270622
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