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The photochemical reaction of benzoquinone with tolan

โœ Scribed by Howard E. Zimmerman; Lawrence Craft

Publisher
Elsevier Science
Year
1964
Tongue
French
Weight
237 KB
Volume
5
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Much of our previous research has concerned Itself with the photochemical behavior of carbonyl containing molecules (3). !l!he present paper deals with our observation of a photochemical reaction of benzoquinone with tolan. Irradiation of benzoquinone (11.0 g.; 0.10 mole) and tolan (18.0 g.; 0.10 mole) in 750 ml. of acetonitrlle under nitrogen, using an ~1i6 high pressure mercury arc and solution filters excluding light below 310 qa, led after 12 hr. to a yellow crystalline product, m.p. 105-106". This product was obtained in 11.8 g. yield after recrystallization from benzene-hexane. The assigned structure I is based on spectral and degradatlve evidence. ThUs the elemental analySiS fit C20&402.

(EtOH) possessed peaks at 262 y (4.32) and 365 and the infrared spectrum had carbonyl bands at 6.08 p, suggesting a highly conjugated system.

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