By Noyes W. A.
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Additional info for A Kinetic Hypothesis to Explain the Function of Electrons in the Chemical Combination of Atoms(en)(5
6'-Neolignans 1. 1a for acuminatin resulted by consideration of spectral data. Trans-isoeugenol and the cis-epoxide prepared from cis-isoeugenol benzoate with m-chloroperbenzoic acid served as model compounds in the structural assignments of the two side chains. 0 Hz). Acuminatin, however, gives rise to a still larger value, due to influence of the biphenyl system. Evidence for placing the two methoxyls on the phenyl ring bearing the propylene oxide group was obtained from MS studies, while the exact location of all three methoxyls was ascertained by Lemieux-von Rudloff oxidation of acuminatin to the epoxy-aldehyde 46 and the biphenyl dicarboxylic acid 47.
An additional technique which yielded structural and stereochemical information in this series involves reduction with sodium in liquid ammonia. This also leads, according to the conditions used, to two types of product, 28, a dihydroguaiaretic acid, and 29, again an aryltetralin. Chart 7 exemplifies the reaction sequence for veraguensin (47). , (CH 2 0Me),. (B) ... Si0 2 chromatography. Chart 7. 8'-neolignans References, pp. 8) (33) (1-6) (A) ... H 2 0 2 , peroxidase. (B) ... J. Chart 8. 8'-neolignans of (E) and (Z)-4-propenylphenols (30; R=H, E or Z; R=OMe, E) to threo-bisquinone methides (31).
Chart 21. 10a) References, pp. 65-72 Neolignans 45 VII. 1' -Neolignans 1. 1a was accorded by consideration of IR, UV and 220 MHz lH NMR spectral data (21). The MS was of little help in the analysis. The rearrangements which seem to account for some of the major peaks could only be formulated with confidence a posteriori (Chart 22). ;h t\ \ '<::::: Pi/""-O ~ t M-30 OMe ~O 1+· ~(--- 0 . 0 Pi o :ccc Pi l+· o l+· ~ Pi. 1a) l+. t ) l+· I __--+-_ Pi I + ~OMe Pi~O~/):O Chart 22. 1a) Interpretation of the MS of a hydrolytic product (59), however, was exempt from such difficulties.