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Azides and Nitrenes. Reactivity and Utility by Eric F. Scriven

By Eric F. Scriven

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T r e a t m e n t with thionyl chloride to form 85 is followed by t r e a t m e n t with b a s e . T h e vinyl azide 86 is formed together with a-chlorostyrene 87 (28). , 89), which lose w a t e r to form 90 (29, 30). , 94 from 91, via 92 and 93) (23). 48 Alfred H a s s n e r 93 94 4. B Y C O N D E N S A T I O N O F A L D E H Y D E S W I T H C*-AZIDO ESTERS OR K E T O N E S This m e t h o d , developed by H e m e t s b e r g e r et al. (31) as a useful synthe­ sis of α-azidocinnamate esters and related c o m p o u n d s , rightfully belongs a m o n g t h e m e t h o d s w h e r e both the C = C and the N function are intro­ d u c e d simultaneously.

Chem. Soc. 103, 3273 (1983); b . A . G. S c h u l t z a n d S. O . M y o n g , J. Org. Chem. 48, 2432 (1983). 47. H . Q u a s t a n d L . , 1485 (1976). 4 8 . D . M . R e v i t t , J. Chem. Soc. Chem. , 24 (1975). 49. A . B . L e v y a n d A . H a s s n e r , J. Am. Chem. Soc. 9 3 , 2051 (1971). 50. J. S. Millership a n d H . S u s c h i t z k y , J. Chem. Soc. Chem. , 1496 (1971). 5 1 . H . W . M o o r e a n d D . S. , 1621 (1971). 52. G. L a n d e n a n d H . W . , 2513 (1976). 5 3 . J . - P .

A . G. S c h u l t z a n d S. O . M y o n g , J. Org. Chem. 48, 2432 (1983). 47. H . Q u a s t a n d L . , 1485 (1976). 4 8 . D . M . R e v i t t , J. Chem. Soc. Chem. , 24 (1975). 49. A . B . L e v y a n d A . H a s s n e r , J. Am. Chem. Soc. 9 3 , 2051 (1971). 50. J. S. Millership a n d H . S u s c h i t z k y , J. Chem. Soc. Chem. , 1496 (1971). 5 1 . H . W . M o o r e a n d D . S. , 1621 (1971). 52. G. L a n d e n a n d H . W . , 2513 (1976). 5 3 . J . - P . L e R o u x , P . - L . D e s b e n e , a n d M .

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