ISSN:
0941-1216
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Azo bridges in compounds 3, 6, 11, 16, 20 and 22 are chemospecifically oxidized with MCPBA to the corresponding azoxy derivatives 4, 7, 12, 17, 21, and 23 in the presence of one or two (20, 22) double bonds even if these are located in a close parallel position to the azo bridge (6, 11, 20, 22). The order of reactivity of different olefinic moieties towards MCPBA was found to be bicycloheptene 〉 bicyclooctene, cyclopentene. Thus, epoxy/azoxides 5, 8, 13, 14, and 19 as well as bisepoxy/azoxides 10 and 15 were obtained. If both the azo and the olefinic bridge are part of a bicycloheptane system (24) the azo group can be no longer oxidized chemospecifically (25 + 26).
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19963380113
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