Pyrolysis of Phenylalkylsulphonyl Azides and 2-Phenethyl Azidoformate. Selectivity of Sulphonylnitrenes and Contrast between Sulphonyl- and Carbonyl-nitrenes

Article abstract of DOI:10.1039/c39810001087

Flash vacuum pyrolysis and solution thermolysis of PhnSO2N3 indicate that intramolecular addition to the phenyl group is preferred in solution, provided that up to an eight-membered sultam ring is formed, otherwise side-chain insertion results, while in the gas phase the latter process is favoured when n = 4, 5, but not 3; some 5,6,7,8-tetrahydroquinoline is obtained when n = 3 at 990 deg C, but 2-phenethyl azidoformate gave monomeric tetrahydro-1,3-oxazino<3,4-a>azepin-2-one and 4-phenyloxazolidinone, but no dihydrocyclopentapyridine, even at 900 deg C.

Full text of DOI:10.1039/c39810001087

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