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Neighboring group participation in photolysis of o-substituted aryls

โœ Scribed by R. Staudenmayer; T.D. Roberts

Book ID
104234758
Publisher
Elsevier Science
Year
1974
Tongue
French
Weight
232 KB
Volume
15
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Acetanilides should fragment and rearrange in ultraviolet light.2 However, if a suitable neighboring group is available in the ortho position other reactions may occur. For example, irradiation of R-cyanoacetanilide, I_, in aqueous solvents provides not only the expected cleavage and rearrangement of the anilide group, but o-acetamidobensamide, in hydration product (see Equation 1).3a Further,photolysis of o-(phenylethynyl) acetanilide, 2, followed by aqueous workup fields 2&y an hydrate, R-acetamidophenyl benzyl ketone. 3b If the workup is interrupted before water is applied 2-methyl-4-beneylidene-4lJ-3,l-beneoxaeine, 2, is isolated (Equation 1).

๐Ÿ“œ SIMILAR VOLUMES

Neighboring group participation in polar
Neighboring group participation in polar bromination of styrene derivatives
โœ Samuel P. McManus; Randy A. Hames ๐Ÿ“‚ Article ๐Ÿ“… 1973 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 163 KB

Recent studies by ingly demonstrated that the benzylic cations (1) rather Fahey and Schneider' and by Yates and Rolston 3y4 have convincpolar bromination of styrene derivatives proceeds through open than cyclic bromonium ions (2). These findings are further supported by the more recent work of Wilki