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By A. F. Bochkov

E-book through Bochkov, Aleksei Feodos Evich

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Example text

Of the e f f e c t of surface a l c o h o l used on t h e The r e a c t i o n s t u d i e d was f o u n d t o b e d r a m a t i c a l l y s o l v e n t - d e p e n d e n t . For example, i n d i e t h y l e t h e r i t g i v e s r i s e to a 1 , 2 - t r a ? i S - g l y c o s i d e , i n t e t r a h y d r o f u r a n to an o r t h o e s t e r , and i n a c e t o n i t r i l e i t d o e s n o t p r o c e e d a t a l l . The r o l e of t h e s o l ­ vent i s e s p e c i a l l y d i f f i c u l t to i n t e r p r e t .

T h e r e f o r e f o r a n y anomer of a h a l i d e t h e s t e r e o c h e m i s t r y of s u b s t i t u t i o n c a n b e d i s t u r b e d b y t h e s e g r o u p s . I n f a c t one can e x p e c t t h e a p p e a r a n c e of a n e q u i l i b r i u m s y s t e m i n c l u d i n g two i s o m e r i c a c y l o x o n i u m i o n s , e a c h o f w h i c h m i g h t l e a d t o a n a l t e r n a t i v e a n o m e r i c p r o d u c t , a s shown i n t h e scheme ( p a g e 33) f o r D - f r u c t o p y r a n o s e d e r i v a t i v e s .

The former u n d e r g o e s r e a c t i o n v i a g l y c o s y l c a t i o n by s p o n t a n e o u s h e t e r o l y s i s o f a C-1 h a l o g e n bond, w h e r e a s f o r t h e l a t t e r t h i s p r o c e s s i s a s s i s t e d by a s i m u l t a n ­ e o u s a t t a c k o f n e i g h b o u r i n g a c y l group a t C-2 t o t h e back s i d e of C - 1 , l e a d i n g t o a cyclic 1,2-acyloxonium ion. Under s i m p l e a l c o h o l y s i s c o n d i t i o n s , s e c o n d a r y a l c o h o l s such as propanol-2 or cyclohexanol induce bimolecular r e a c t i o n , F o r t h e former t h e e n t r o p y of a c t i v a t i o n (-48 e , u , ) was i n c o m p a t i b l e w i t h a monomole­ cular process, The a l c o h o l y s i s o f a c y l g l y c o s y l h a l i d e s i n t h e p r e s e n c e of a s o l u b l e e l e c t r o p h i l i c c a t a l y s t ( H g C l 2 a n d H g B r 2 a r e t h e m o s t common m o d e l s ) i s e x a c t l y b i m o l e c u ­ l a r ( f i r s t o r d e r i n g l y c o s y l h a l i d e and f i r s t o r d e r i n c a t a l y s t ) .

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