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Steric effects on the conformation of valerolactones

โœ Scribed by R.N. Johnson; N.V. Riggs


Publisher
Elsevier Science
Year
1967
Tongue
French
Weight
179 KB
Volume
8
Category
Article
ISSN
0040-4039

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โœฆ Synopsis


Apa& iron iMidmlt8l oboom3tloM, tho oonfomtion of 6 -laotone haa, am far u m are avuw, been the aubjeot of thme gmnecalintiolur (1,2,3). Althou& Nathieaon (1) Momed gemrally the boat oonformation, more reoontl~"noIm8l" oarbo~l-etrot~frquulo%o~ near174oom-' In solutlonhavo boenoorrelatodwithhalf-ohalr oonfonmtlons inthe nolid ntate by x4-q w~ia, url %I&" value0 naar 1760 on-' In solution have boon oonnlated with boat oo&omatiozm in the solid atate by X-ray analymlo, orgoomtrioal rquirmmtr inbridgadsysta~~ (2). Hostreoentlyoptloal rotrtorJrdispor8ionmmumme nts onoptioal~aotlve 6-l8atone6 decked from aaturc+l produota of kno8n oonfigrmtlon have been oorrelatad on the ba8i.a that the &-laotone *adopta abortoonformationunle~~ oertti dOEi iDtO~tiOE8 873 Fdi0V.d in (L --Oh&l' OOlliOrnStiOB (3).


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It has recently been argued [1,2] that the barrier to rotation around the C ร€ C bond in ethane is not to be explained by the generally accepted picture of steric hindrance between vicinal Cร€H bonds in the eclipsed conformation but is caused by more favorable orbital interaction in the staggered conf