Abstract
Chlorination of 2-methallyl chloride ( 9) and subsequent treatment with sodium iodide leads to 3-iodo-2-iodomethyl-1-propene ( 6), which is converted to 4-methylene-1,6-heptadiyne ( 10) on reaction with ethynylmagnesium bromide in the presence of cuprous chloride. The bis-Grignard derivative of 10 on treatment with the diiodide 6 in the presence of cuprous chloride gives 4,9,14,19-tetramethylene- 1,6,11,16-cycloeicosatetrayne ( 16), a 20-membered ring cyclic tetraacetylene. Oxidative coupling of the diacetylene 10 with oxygen, cuprous chloride and ammonium chloride leads to 6,13-dimethylene-1,3,8,10- cyclotetradecatetrayne, a 14-membered ring cyclic tetraacetylene.
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