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Extra resources for Topics in Stereochemistry, Volume 10

Example text

Consequently it was suggested (35) that to discuss such cases in terms of well-defined "envelopes" or "half-chairs" with "equatorial" or "axial" substituents probably leads to gross oversimplification and, in the hands of the uninitiated, to erroneous interpretations. C. 0]decane (perhydroa z u l e n e s 1 6 , 1 7 ) (37). Boyd and co-workers (37) have used f o r c e - f i e l d c a l c u l a - t i o n s w i t h energy minimization t o i n v e s t i g a t e , among o t h e r compounds, s t r a i n e d c y c l i c hydrocarbons, t h e c r i t e r i o n o f s u c c e s s b e i n g , a s i s u s u a l l y t h e c a s e , t h e agreement of c a l c u l a t e d h e a t s o f formation (hence s t r a i n e n e r g i e s ) w i t h e x p e r i mental v a l u e s ( s e e Table 4 f o r s t r u c t u r a l p a r a m e t e r s ) .

Benzion Fuchs 53 t h a t such simple c o r r e l a t i o n s (185) a r e probably i n e r r o r , due t o t h e a l r e a d y mentioned d e p a r t u r e from t r i g o n a l symmetry i n such systems. Conformational arguments have a l s o been used i n chemical s t u d i e s , such a s t h e s t e r e o c h e m i s t r y of e n o l i z a t i o n of 1 7 - k e t o s t e r o i d s (186b) and t h e e q u i l i b r a t i o n of 2-hydroxyA-norcholestanol ( 1 8 9 ) . E x t e n s i v e ORD and CD s t u d i e s of A-nor and D-ring k e t o n e s have been performed (190) w i t h r e a s o n i n g a l o n g l i n e s s i m i l a r t o t h o s e used by Ouannes and Jacqy$s f o r s u b s t i t u t e d c y c l o pentanones ( 3 9 ) .

The trans-lI2-dihalogen compounds 57 seem to prefer "diaxial" conformations (159a,b). The epimeric 1-indanols have also been studied (159~). 5 7 E. 0]hexane (11). Its basic conformation is imposed to the extent that the fusion must be cis and the fivemembered ring constrained to an envelope, but it can, in principle, choose between a chair or a boat conformation. It turns out that the latter is the actual form of occurrence for virtually all derivatives (58-65) that have been investigated structurally.

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