ISSN:
0009-2940
Keywords:
1,2-Cyclooctadiene
;
1-Methyl-1,2-cyclooctadiene
;
Allene, dimerization
;
Carben, addition to cycloallenes
;
Gas chromatography, chiral
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
“Dimerization Products” of 1,2-Cyclooctadiene?The conversion of 8,8-dibromobicyclo[5.1.0]octane (2) with methyllithium is known to yield kinetically labile 1,2-cyclooctadiene (1). This strained cyclic allene readily dimerizes at ambient temperature. The 1-methyl derivative enjoys greater kinetic stability, but nevertheless only three [2 + 2]-cycloaddition products can be isolated after workup. Whereas the dimerization products 17, 22, 23, 24 can be predicted from recent studies, the carbene adducts 15 and 16 were not yet reported. The stereochemistry of 17 and 22 is determined by X-ray structure analysis of their Diels-;Alder adducts with tetracyanoethylene.
Additional Material:
3 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19931260124
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