Issue 3, 1976

Generation and interception of isobenzofurans from 2-(α-bromoalkyl)benzophenones

Abstract

2-(Bromomethyl)benzophenone, prepared by side-chain bromination of 2-methylbenzophenone, is converted into naphthalene derivatives [(2), (4), and (5)] by heating in tetrachloromethane with olefinic or acetylenic dienophiles. A mechanism is suggested in which 1-phenylisobenzofuran is generated by displacement of bromide by the neighbouring carbonyl group; the isobenzofuran then undergoes cycloaddition and the cycloadducts are aromatised by the hydrogen bromide present. Similar reactions are observed with 2-(2-bromoethyl)benzophenone, but in this case the primary Diels–Alder adducts (7) and (8) can be isolated. Similarly, (Z)-4-bromo-1,3-di-phenylbut-2-en-1-one (9) is converted into 2,4-diphenylfuran by heating in ethanol.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1976, 336-338

Generation and interception of isobenzofurans from 2-(α-bromoalkyl)benzophenones

R. Faragher and T. L. Gilchrist, J. Chem. Soc., Perkin Trans. 1, 1976, 336 DOI: 10.1039/P19760000336

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