By Ernest L. Eliel, Samuel H. Wilen, Norman L. Allinger
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Additional resources for Topics in Stereochemistry, Volume 10
What appears clear is that these compounds, and specifically cyclopentene, occur as severely restricted pseudorotators in an envelope form, with a flap inversion barrier of <1 kcal/mol. Microwave (MW) spectra qualitatively confirm this situation (153,154) and lead to an estimate of the puckering ' . (out-of-plane) angle of 22 2 2 ED studies (155) indicate a puckering angle of 29 ? 0'. Attempts to gain conformational information from vinylallylic proton spin coupling were only qualitatively successful (156).
L]). 435 fi (73) 32 Conformations of Five-Membered Rings dynamic conformational a n a l y s i s . The five-membered r i n g i s no exception t o t h i s a s s e r t i o n although t h e r e a r e some r e s e r v a tions. 51 ppm ( C C l 4 ) ( 7 4 ) . I t s t a n d s t o r e a s o n t h a t no DNMR s t u d y i s p o s s i b l e i n t h i s case due t o t h e low b a r r i e r (near kT) t o p s e u d o r o t a t i o n ( v i d e s u p r a ) ( 6 9 ) . Anbther primary o b j e c t i v e i s , however, c o r r e l a t i o n of v i c i n a l coupling c o n s t a n t s w i t h d i h e d r a l a n g l e s .
Bucourt and Hainaut (38) calculated, inter alia, c i s - and trans-hydrindane geonetries by plotting the energies of the six-membered ring in conjunction with those of the five-membered one with small torsional gradients. , however refs. 11 and 53). For the best-known fused cyclopentane system, ring D of steroids, extensive theoretical and experimental efforts have yielded a rather detailed understanding of its conformational features. Brutcher and Bauer (41a) had adopted essentially a Pitzertype approach in evaluating energies, using maximally puckered cyclopentane models.