ChemInform Abstract: NMR EXPERIMENTS ON ACETALS PART 48, THE PRINS‐REACTION ON CYCLIC (POLY)OLEFINS AND THE CHARACTERIZATION OF RESULTING 1,3‐DIOXANES

Abstract

Abstract.W e h a v e i n v e s t i g a t e d t h e P r i n s -r e a c t i o n of formaldehyde on s e v e r a l c y c l i c ( p o 1 y ) o l e f i n s . The n a t u r e (100 and 300 M H z m s t u d i e s ; t a h l e 11) and y i e l d s of t h e r e s u l t i n g 1 . 3 -d i o x a n i c compounds have b e e n c a r e f u l l y a s s e s s e d ( T a b l e I ) . The r e s u l t s i n d i c a t e t h a t m o s t p r e v i o u s c l a i m s a r e t o be t a k e n q n l y a s g e n e r a l r u l e s , w i t h many e x c e p t i o m h o w e v e r . Thus, a wide v a r i e t y i n s t e r e o s p e c i f i c i t y of t h e p r i m a r y r e a c t i o n must be a c c e p t e d , l e a d i n g t o s y n and a n t i ( d i a x i a l ) and even t r a n s ( d i e q u a t o r i a l ) a d d i t i o n r o u t e s .