Solution and flash vacuum pyrolyses of 3-arylpropanesulfonyl and 2-(aryloxy) ethanesulfonyl azides. Synthesis of 7-and 8-membered sultams

RA Abramovitch, AO Kress, SP McManus…

Index: Abramovitch, Rudolph A.; Kress, Albert O.; McManus, Samuel P.; Smith, Maurice R. Journal of Organic Chemistry, 1984 , vol. 49, # 17 p. 3114 - 3121

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Citation Number: 17

Abstract

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 structures of the 7-membered sultams have been established ...

~3%

Detail

~2%

Detail

~48%

$2-oxa-5$l^{6}-thia-6-azabicyclo[5.4.0]undeca-7,9,11-triene 5,5-dioxide Structure$

$2-oxa-5$l^{6}-thia-6-azabicyclo[5.4.0]undeca-7,9,11-triene 5,5-dioxide Structure$

~96%

~1%

~84%

Pyrolysis of phenylalkylsulphonyl azides and 2-phenethyl azi...

[Abramovitch, Rudolph A.; Hendi, Shivakumar B.; Kress, Albert O. Journal of the Chemical Society, Chemical Communications, 1981 , # 20 p. 1087 - 1088]