Studies in alkyl-oxygen fission : some reactions of methyl 9-anthryl carbinol and 2-fluorenyl phenyl carbinol (1) ; The partial resolution of (+/-) -2 nitro 9-fluorenol (2)

• Main Author: Friedler, Leo
• Published: University of Surrey 1952
• Online Access: https://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.751464

(1) Studies in alkyl-oxygen fission. Some reactions of methyl 9-anthryl carbinol and 2-fluorenyl phenyl carbinol. (2) The partial resolution of (+/-) 2-nitro 9-fluorenol. The alkyl-oxygen fission mechanism of carboxylic esters of certain secondary alcohols is briefly summarised. A discussion is given of modern theories regarding the reactivity of polynuclear aromatic groupings with special reference to the alkyl-oxygen fission reactivity of some esters of methylphenyl, methyl l-naphthyl, methyl 2-naphthyl and methyl 9-anthryl carbinols. Several esters of methyl 9-anthryI carbinol have been shown to undergo alkyl-oxygen fission reactions similar to the corresponding esters of methyl 2-naphthyl carbinol. The complete resolution of methyl 9-anthryl carbinol has been effected by means of the brucine salts of its hydrogen phthalate, and constitutes the first resolution described in the literature of a secondary alcohol containing the 9-anthryl grouping. From a study of some reactions of 9- and 2-fluorenyl phenyl carbinols it has been found that whereas the 9-fluorenyl grouping inhibits alkyl-oxygen fission, the 2-fluorenyl grouping aids this mechanism. some cleavage reactions of sulphones are discussed, and the reduction of several di-aryl sulphones by means of sodium amalgam and also Raney nickel catalyst are described. A short review of the stereochemistry of fluorene is given, and the partial resolution of (+/-) 2-nitro 9-fluorenol by the separation of the l-menthoxyacetate esters is described.