ISSN:
0009-2940
Keywords:
Anthracenes
;
Oxyallyl cations
;
Ketones, α,α'-oligobromo-
;
Dibenzohomobarrelenes
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Sonication of a zinc/copper couple, N,O-bis(trimethylsilyl)-acetamide (BSA) and α,α'-oligobromo ketones in benzene gives rise to oxyallyl intermediates which cycloadd to anthracene. Starting from 1,1,3,3-tetrabromoacetone (2a) and anthracene (1a), we obtained 11,11,13-tribrominated adduct 4 as the major product (42%). The expected 11,13-dibrominated adduct trans-3 was formed as a minor product (5%), but it became the main product when the known oxyallyl methodology was applied. Dibenzohomobarrelenes 9 and 17 were prepared by short routes.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19941270927
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