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Similar b e h a v i o r is o b s e r v e d for the methyl eis a z i d o c i n n a m a t e 114f (41). T h e fluorinated vinyl azide 127 is unstable at r o o m t e m p e r a t u r e and is c o n v e r t e d to azirine 128 (42). 54 Alfred H a s s n e r r Ph 114e f Ph x R: Ph 115 R:C0 Me 2 NaN, (CF ) C=C-F (CF ) C=C-N OMe OMe 3 3 2 2 3 (CF OMe VI 128 127 a - A z i d o - a , ß - u n s a t u r a t e d k e t o n e s 129, w h e n t h e r m o l y z e d , afford azirines 130 (R = alkyl), but they d e c o m p o s e to rearranged nitriles 131 Ph-C II 0 Ph-C II 0 129 130 R:Ar NC-CH-C-Ph I R II 0 131 w h e n R = aryl (43, 44).

R. F o r r e s t e r , Μ . M . Ogilvy, a n d R. H . T h o m s o n , J. Chem. Soc. Chem. , 483 (1972). 32. P . J. W a g n e r a n d B . J. S c h e v e , J. Am. Chem. Soc. 101, 378 (1979). 33. a. W . K u h n a n d E . Knopf, Z. Phys. Chem. Abt. Β 7, 292 (1930); b . G. B a l a v o i n e , A . M o r a d p o u r , a n d H . K a g a n , / . Am. Chem. Soc. 96, 5152 (1974). 34. L . E . F i k e s a n d H . , 2525 (1976). 35. a. M . P . D o y l e a n d W . W i e r e n g a , / . Am. Chem. Soc. 94, 3896 (1972); b .

Soc. 94, 3896 (1972); b . M . P . D o y l e a n d W . W i e r e n g a , ibid. 94, 3901 (1972); c. R. H . M c G i r k and Ε . H . W h i t e , ibid. 95, 3805 (1973); d. M . P . D o y l e , D . M . H e d s t r a n d , S. C. B u s m a n , a n d D . A l e x a n d e r , ibid. 97, 5554 (1975). 36. a. A . S u z u k i , S. S o n o , M . I t o h , H . C. B r o w n , a n d Μ . M . M i d l a n d , / . Am. Chem. Soc. 9 3 , 4329 (1971); b . H . C. B r o w n , Μ . M . M i d l a n d , a n d A . B . L e v y , ibid.

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