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1,5‐Cyclooctadiyne. Preparation and Reactivity
Author(s) -
KlosterJensen Else,
Wirz Jakob
Publication year - 1975
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19750580121
Subject(s) - chemistry , cyclooctatetraene , reactivity (psychology) , adduct , yield (engineering) , 1,3 butadiene , base (topology) , ring (chemistry) , exothermic reaction , polymerization , ring strain , photochemistry , medicinal chemistry , organic chemistry , polymer chemistry , catalysis , molecule , medicine , mathematical analysis , materials science , alternative medicine , mathematics , polymer , pathology , metallurgy
1,5‐Cyclooctadiyne 1 was isolated in 2 percent yield from polymerized butatriene 5 . Other oligomers of 5 were detected in the reaction mixture by combined GLC./MS. analysis but have not been identified. Diels ‐ Alder adducts of 1 with two equivalents of 1,3‐butadiene and of 2,3‐dimethyl‐1,3‐butadiene have been prepared. In the presence of strong base 1 isomerized to cyclooctatetraene. 5 was reformed by photolysis of 1 . Attempts to prepare transition metal complexes of 1 failed. Effects of ring strain and of transannular interaction on the reactivity of 1 are discussed. The dimerization of 5 to 1 is predicted to be strongly exothermic.