Abstract
The synthesis and
solvolytic behaviour (in buffered acetic acid) of the p-nitrobenzenesulphonate
esters of 2-cyclooctatetraenylethanol, 3- cyclooctatetraenylpropan-1-ol and
4-cyclooctatetraenyl-butan-1-ol are described. For comparison with the
cyclooctatetraenylalkyl derivatives, kinetic data for the corresponding
ω-(cyclooct-1?-enyl)alkyl and ω- cyclooctyl p-nitrobenzenesulphonates
are reported. ��� Kinetic and product studies have shown that
π-bond participation occurs in the acetolysis of 2-cyclooctatetraenylethyl
p- nitrobenzenesulphonate. The nature of the cyclized products, which amount to
95 % when 1.1 equiv. of sodium acetate (the buffer) are used, depends markedly
on the concentration of buffer. ��� Acetolysis of 3-cyclooctatetraenylpropyl
p-nitrobenzenesulphonates gives at least 98% non-cyclized products. A probable
cyclized product (<2%) is tentatively identified as bicyclo[6,3,0]-undeca-1,3,5,7-
tetraene. ��� Cyclized products (44%) are formed in the
acetolysis of 4- cyclooctatetraenylbutyl p-nitrobenzene-sulphonate.
Cited by
11 articles.
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