Tetrahedron p. 4129 - 4135 (1974)
Update date:2022-08-02
Topics:
Caccamese
Montaudo
Recca
Fringuelli
Taticchi
Computer simulation of the lanthanide induced shifts has been applied to study of the conformational preferences in the 2-formyl and 2-acetyl derivatives of furan, thiophene, selenophene and tellurophene. The results assign a nearly equipopulated mixture of s-cis and s-trans conformers to the furan, and a preponderance of the s-trans form to the thiophene, selenophene and tellurophene derivatives. This difference is interpreted as due to the interaction between the heteroatom and carbonyl oxygen lone pairs. The 2-N,N-dimethylcarboxyamide derivatives of furan, thiophene and selenophene are found to exist mainly in a quasi-planar s-cis form. The barriers to the rotation about the amide bond in these amides have been measured and related to the electronegativity of the heteroatom.
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Doi:10.1246/cl.1975.323
(1975)Doi:10.1016/j.steroids.2013.09.011
(2013)Doi:10.1016/S0960-894X(97)00442-3
(1997)Doi:10.1021/ol034408n
(2003)Doi:10.1002/jlcr.670
(2003)Doi:10.1021/ja01241a007
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