Sc(OTf)3-catalyzed Cyclooligomerization of 2,4-Dialkoxybenzyl Alcohols. Formation of Resorcin[n]arene Peralkyl Ethers

doi:10.1007/S00289-004-0323-8

Paper

Sc(OTf)3-catalyzed Cyclooligomerization of 2,4-Dialkoxybenzyl Alcohols. Formation of Resorcin[n]arene Peralkyl Ethers

Published 2005 · Osamu Morikawa, Tomonori Ishizaka, Hijiri Sakakibara

Polymer Bulletin

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11

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Abstract

SummaryThe cyclooligomerization of 2,4-dialkoxybenzyl alcohols 3 catalyzed by Sc(OTf)3 in CH3CN under high dilution conditions produced a series of resorcin[n]arene peralkyl ethers containing four to nine resorcinol units. When the reactions were conducted at 50°C, the cyclic tetramers 4, which are thermodynamically favored products, are selectively formed in good yields. It is noteworthy that the reaction of 2,4-dimethoxybenzyl alcohol 3d at 0°C produced the corresponding cyclic octamer 8d as the major product. In other cases, such as the selective formation of a cyclic octamer could not be observed. This selective formation of 8d is due to a combination of the reversibility of the oligomerization in the presence of 3d and the insolubility of the octamer in the reaction medium. The conformational analysis of these cyclic oligomers was done by variable temperature 1H NMR spectroscopy.

Study Snapshot

Sc(OTf)3-catalyzed cyclooligomerization of 2,4-dialkoxybenzyl alcohols produces resorcin[n]arene peralkyl ethers with thermodynamically favored products, such as cyclic tetramers,

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Sc(OTf)3-catalyzed Cyclooligomerization of 2,4-Dialkoxybenzyl Alcohols. Formation of Resorcin[n]arene Peralkyl Ethers

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References

Sc(OTf)3-catalyzed cyclocondensation of 2-propylresorcinol with diethoxymethane. Formation and fragmentation of resorcin[n]arenes

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Citations

Improved Synthesis of Larger Resorcinarenes.

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