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Nuclear deuterium exchange in methoxybenzenes and methylated flavonoids

✍ Scribed by G. F. Kolar

Publisher
John Wiley and Sons
Year
1971
Tongue
French
Weight
296 KB
Volume
7
Category
Article
ISSN
0022-2135

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✦ Synopsis

The isolation of 6,8-d~-catechinlepicatechin 5,7,3',4'-tetramethyI ether from the cleavage of a methylated condensed procyanidin with 0 2 Oldioxan resulted in an investigation of deuterium exchange in some related compounds under identical experimental conditions.

In the absence of any acidic catalyst, a partial exchange was established in the majority of di-and trimethoxybenzenes when heated with DZOldioxan (3: 1) at 9.50 for 16 hr in Pyrex glass ampules; 1,3,5-trimethoxybenzene was found to undergo a complete exchange of nuclear hydrogens under these mild conditions. Methylated javonoids containing a reactive phloroglucinol system also exchanged both nuclear hydrogens at c 6 and c 8 with deuterium, but 5,7,3',4'-tetramethoxy-2,3-trans-~avan-3,4-cis-diol (2 R : 3 R-trans--R3 : IS-cis) failed to react.

INTRODUCTION.

Condensed procyanidins of the general structure I are degraded into their constituent units by treatment with hot mineral acids, and the cleavage can be represented by the following mechanism :

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