80639-72-1Relevant academic research and scientific papers
Solution and Flash Vacuum Pyrolyses of 3-Arylpropanesulfonyl and 2-(Aryloxy)ethanesulfonyl Azides. Synthesis of 7-Membered Sultams
Abramovitch, Rudolph A.,Kress, Albert O.,McManus, Samuel P.,Smith, Maurice R.
, p. 3114 - 3121 (2007/10/02)
The solution and flash vacuum pyrolyses of 3-arylpropanesulfonyl azides have been studied and the results compared with those of the corresponding 2-arylethanesulfonyl azides.The best yields of 7-membered ring sultams are formed on solution decomposition in Freon 113.Hydrogen abstraction and solvent insertion products are obtained mainly in hydrocarbon solvents.The structure of the 7-membered sultams have been established unambiguously and an authentic sample of the parent 2,3,4,5-tetrahydro-1,2-thiazepine 1,1-dioxide prepared.Decomposition of 3-(2,6-dichlorophenyl)propanesulfonyl azide (22) leads to a 6,9-dichloro sultam (33c) via a 1,2-chlorine shift.FVP of 3-(2-mesityl)propanesulfonyl azide (20) gave a good yield of the 7-membered ring sultam (34)(1,2-methyl shift).FVP of 3-phenyl-1-propanesulfonyl azide (16) at 995 deg C (0.05 mm) gave, among other products, a 6.2percent yield of 5,6,7,8-tetrahydroquinoline (39).The formation of these products is discussed.Thermolysis of 2-(aryloxy)ethanesulfonyl azides gave the corresponding 7-membered ring sultams 27 as well.
Pyrolysis of Phenylalkylsulphonyl Azides and 2-Phenethyl Azidoformate. Selectivity of Sulphonylnitrenes and Contrast between Sulphonyl- and Carbonyl-nitrenes
Abramovitch, Rudolph A.,Hendi, Shivakumar B.,Kress, Albert O.
, p. 1087 - 1088 (2007/10/02)
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-oxazinoazepin-2-one and 4-phenyloxazolidinone, but no dihydrocyclopentapyridine, even at 900 deg C.
