CYCLIZATION OF DIALKYL(3-PHENYLPROPEN-2-YL)(3-PHENYLPROPYN-2-YL)AMMONIUM BROMIDES BY THE ACTION OF AN AQUEOUS ALKALI SOLUTION. AQUEOUS-ALKALINE CLEAVAGE OF THE CYCLIZATION PRODUCTS – N , N -DIALKYL-4(9)-PHENYL-3a,4-DIHYDROBENZO[ f ]ISOINDOLINIUM BROMIDES

Abstract

When heated in an alkaline aqueous medium, dialkyl(3-phenylpropen-2-yl)(3-phenylpropyn-2-yl)- ammonium bromides undergo intramolecular cyclization, forming N,N -dialkyl-4(9)-phenyl-3a,4-dihydrobenzo[ f ]isoindolinium bromides. The cyclization products undergo aqueous-alkaline cleavage at the C(1)–N(2) or N(2)–C(3) bond, which leads to a mixture of 2-(dialkylaminomethyl)-3-methyl- and 3-(dialkylaminomethyl)-2-methyl-1-phenylnaphthalenes. However, only the C(1)–N(2) bond cleavage product is formed in the case of 2,2-pentamethylene-9-phenyl-3a,4-dihydrobenzo[ f ]isoindolinium bromide. Authors: E. O. Chukhajian, L. V. Ayrapetyan, El. O. Chukhajian, and H. A. Panosyan English Translation in Chemistry of Heterocyclic Compounds, 2012, 48 (9), pp 1314-1320 http://link.springer.com/article/10.1007/s10593-012-1138-4