Ch0

NMe2

NMe2

nch3

nch3

nch3

nch3

ch3

ing compound 3,4-dihydro-1 -methyl-2( 1H) naphthalenone (13) already containing the tetrahydronaphthalene skeleton of (9) initially gave lower yields(5) than the longer method. However, significant improvement of the shorter sequence was subsequently achieved")" (see also ref. 19). This method of synthesis was first reported by Barltrop(6) who suggested the name 6,7-benz-morphan (later changed to benzomorphan by the editors of the Journal of Organic Chemistry) for a class of compounds corresponding to (4). Barltrop used 2-chloro-iV,iV-diethylethylamine rather than the 7V,7V-dimethyl derivative in the alkylation of (13) and did not take his synthesis beyond the stage represented by the quaternary compound (12).

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