Issue 0, 1972

Some derivatives of 5,6,11,12-tetrahydrodibenzo[b,f][1,4]diazocine

Abstract

The synthesis of 5,6,11,12-tetrahydro-12-p-tolylsulphonyldibenzo[b,f][1,4]diazocin-6-one and a number of 5-alkyl derivatives is described. Removal of the p-tolylsulphonyl group from these compounds with sulphuric acid was accompanied by a ring contraction, the products being phthalimidines. The 5-methyl derivative (IIb) also gave a phthalimidine when treated with phenyl-lithium. The reduction of the dibenzodiazocines was investigated. An authentic sample of 5,6,11,12-tetrahydro-5-methyldibenzo[b,f][1,4]diazocine was prepared, and a compound to which this structure was previously assigned was shown to be the bis-(12-methyldiazocin-5-yl)methane (XVII). In an attempted synthesis of 11-substituted 5,6-dihydrodibenzo[b,f][1,4]diazocines the only products obtained were substituted benzimidazoles.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1972, 1964-1971

Some derivatives of 5,6,11,12-tetrahydrodibenzo[b,f][1,4]diazocine

A. Saunders and J. M. Sprake, J. Chem. Soc., Perkin Trans. 1, 1972, 1964 DOI: 10.1039/P19720001964

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