Interactions gauches et chemins réactionnels. Etudes conformationnelles d'hydroxyalkyl-4 cyclohexènes contraints
Keyword(s):
From J and δ values determined by the nmr study of alcohols obtained by addition of CH3Li and LiAlH4 to the exocyclic carbonyl of cis and trans 3-alkyl 4-carbomethoxy (or acetyl) cyclohexenes (alkyl = H, CH3, C(CH3)3), we have deduced the conformational free energy values (ΔG0X) of the CH(CH3)OH and C(CH3)2OH substituents (0.62 and 2.08 kcal mol−1 respectively) as well as the values for some related conformational equilibria. For transtert-butyl derivatives the stability of the diaxial conformer agrees with a reaction path involving high energy conformers.
1967 ◽
Vol 45
(23)
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pp. 2955-2961
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1985 ◽
Vol 63
(10)
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pp. 2747-2751
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1985 ◽
Vol 50
(7)
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pp. 1594-1601
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2010 ◽
Vol 24
(3-4)
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pp. 349-353
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1976 ◽
pp. 278-279
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