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ChemInform Abstract: 6,6-Dimethyl-4,8-dioxospiro[2,5]octane-1,1,2,2-tetracarbonitrile in Synthesis of Heterocyclic Compounds of 2,3-Dihydrofuran and 5,6,7,8-Tetrahydro-4H-chromene Series.

✍ Scribed by O. V. KAYUKOVA; P. M. LUKIN; YA. S. KAYUKOV; O. E. NASAKIN; V. N. KHRUSTALEV; V. N. NESTEROV; M. YU. ANTIPIN

Publisher: John Wiley and Sons
Year: 2010
Weight: 35 KB
Volume: 29
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199832176

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✦ Synopsis

octane-1,1,2,2-tetracarbonitrile in Synthesis of Heterocyclic Compounds of 2,3-Dihydrofuran and 5,6,7,8-Tetrahydro-4H-chromene Series.

-Reaction of tetracyanoethylene (I) with 2-bromodimedone (II) affords the tetracyanospiro[2.5]octane (III) in high yield. On reaction with alcohols or oximes (IV), a recyclization is observed producing the dihydrofurans (V). Nucleophilic attack of triarylphosphines (VI) to the cyano groups results in a cyclopropane ring opening and recyclization to the tetrahydrochromene derivatives (VII) or (VIII). -

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