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3,7,10,14-tetrasubstituted 1,8-didehydro[14]annulens

✍ Scribed by Kunisuke Fukui; Tateo Nomoto; Shin'ichi Nakatsuji; Masazumi Nakagawa

Publisher: Elsevier Science
Year: 1972
Tongue: French
Weight: 199 KB
Volume: 13
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)93991-7

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✦ Synopsis

1,8-Didehydro[l&]annulene (XII) is an unusually stable and highly aromatic annulene prepared and extensively investigated by F. Sondheimer and his coworkers (1). The dienyne ketones (II and IX) obtained from enyne aldehydes (I and VIII), key intermediates in the syntheses of tetrasubstituted tetradehydro[18]annulenes (2, 3),appeared to be potential precursors of the present syntheses of tetrasubstituted 1,8-didehydro[l&]annulenes. The unsymmetrical dienyne ketones (V9 pale yellow crystals, mp 75.5-76.20~. Found: C, 85.91; H, 7.64%. Calcd. for C17H1eO: C, 85.67; H, 7.61%) was prepared by the condensation of pinacolone with I. After several experimentations 9 cyclic dimerisation of dienyne ketones (II, V and IX) to yield l&-membered cyclic glycols (III , VI and X) could be realieed I: R=Ph VIII: R= But R=R'=Ph -..

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