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The photochemical anti-markovnikov addition of methanol to an acyclic olefin

✍ Scribed by Stephen S. Hixson

Publisher: Elsevier Science
Year: 1971
Tongue: French
Weight: 163 KB
Volume: 12
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)97502-1

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✦ Synopsis

Observations of the photochemical polar addition of methanol to olefins have hereto-Pore been restricted to cases where the double bond is contained within a ring' or (in a few examples) where an acyclic double bond is conjugated to a highly polar carbonyl grou~.~ We wish to report the anti-Markovnikov photochemical addition OP methanol to an acyclic olefin not conjugated with any highly polar group, an addition, therefore, quite diPPerent Prom those previously reported. Irradiation3 of a 2.I.6 x 10m3 g methanol solution of t~-3-(_pcyanophenyl)~l-phenyl-propene4 (5) for 320 min provided in addition to 407 of a mixture of sand tranr-1, 13$ -_ of a mixture of cis--and t~s-l-(p-cyanophenyl)~-~enylcyclopropsn (c), and l.8$ of -_ l-(p_cyanophtnyl)-2-methoxy-j-phenylpropam (2). Unidentified higher molecular weight materials and very small amounts (4%) of photochemical products of 2, account Por the remaining material.

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