- Synthesis of 1,6-diethynylcyclohepta-1,3,5-triene and its oxidative coupling to dimethano-bridged octadehydroannulene and trimethano-bridged dodecadehydroannulene
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1,6-Diethynylcyclohepta-1,3,5-triene 27 was synthesized from 1,6-diacetylcyclohepta-1,3,5-triene 24.Oxidative coupling of the diacetylene 27 with copper(II) acetate in pyridine (Eglinton conditions) led to the cyclic 'dimer', a dimethano-bridged octadehydroannulene 28, in 18percent yield and the cyclic 'trimer', a trimethano-bridged dodecadehydroannulene 29, in 19percent yield.Both compounds 28 and 29 consisted of an equilibrating mixture of two conformers which differed in the relative disposition of the methano bridges.Oxidative coupling of compound 27 with oxygen, copper(I) chloride and ammonium chloride (Glaser conditions) afforded 2,3,4,5-tetrachloro-1,6-methanoannulene 32 in 3.5percent yield together with compounds 28 and 29.
- Ojima, Juro,Daimon, Tomoyo,Hiraiwa, Naoki,Higuchi, Hiroyuki,ueno, Masako,Yamamoto, Gaku
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p. 2795 - 2802
(2007/10/02)
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