ISSN:
0009-2940
Keywords:
Photochemistry
;
Stereoselective bromination
;
Deoxygenation
;
Allyl-Cyclopropyl ring closure
;
2D-NMR
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Synthesis of Medium and Large Rings, XXXVI. - Synthesis of a Bridged Bicyclo[2.1.0]pentane Derivative with inside ConfigurationDihydrocyclobutafurans 4 (H instead of Br) are reactive intermediates in the photochemical rearrangement of 3,6-hexanooxepine-4,5-dicarboxylic esters. The synthesis of the bromo derivative 4 was achieved by irradiation of the epoxyoxepine 1 followed by a regio- and stereoselective NBS bromination of 2 and deoxygenation of 3 with tungsten hexachloride/n-butyllithium. Treatment of the allylic bromide 4 with sodium methoxide gave surprisingly the title compound 5. The structure of 5 was established by thorough NMR analysis.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19941270714
Permalink
