Steric effects of methoxy-groups in some biphenyls derived from thebaine. Part I. Unbridged biphenyls

1 January 1971

journal article
research article
Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society C: Organic

p. 323-328
https://doi.org/10.1039/j39710000323

Abstract

Optically active 3,4-dimethoxy-2-(5-methoxy-2-vinylphenyl)stilbene (III) and 2′-ethyl-5,6,5′-trimethoxy-2-(β-phenethyl)biphenyl (IV) have been prepared from thebaine and their racemisation has been studied. Compound (IV) and the closely related compound (V) are highly optically stable (E_rac 34 kcal mol^–1). The stilbene (III) racemises more readily (E_rac 27·8 kcal mol^–1). Their u.v. spectra and optical stabilities are discussed.

Keywords

THEBAINE
BIPHENYLS
OPTICAL STABILITIES
KCAL MOL
TRIMETHOXY
READILY
U.V
SPECTRA

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