Products Cited in Publications Worldwide Stereospecific single step cyclization to give belt-functionalized pillar[6]arenes

Stereospecific single step cyclization to give belt-functionalized pillar[6]arenes

Coady, Zeke; Smith, Jordan N.; Wilson, Katie A.; White, Nicholas G.

DOI:

Abstract

Two macrocycles were synthesized through cyclization reactions of 1-(2,5-diethoxyphenyl)ethan-1-ol and 1-(2,5-dimethoxyphenyl)ethan-1-ol giving pillar [6]arenes with a Me substituent at each belt position. These macrocycles form stereospecifically with the only observed isomer being the rtctct isomer with alternating up and down orientations of the belt Me groups. Isolated yields were modest (7 and 9%) but the macrocycles are prepared in a single step from either a com.-available alc. or very readily-prepared precursor. X-ray crystal structures of the macrocycles indicate they have a capsule-like structure, which is far from the conventional pillar shape. D. functional theory calculations reveal that the energy barrier required to obtain the pillar conformation is significantly higher for these belt-functionalized macrocycles than for the conventional belt-unfunctionalized pillar[6]arenes.

Keywords

pillararenes ; supramolecular chemistry ; synthesis ; macrocycles

Purchased from AmBeed

A1119159120523-13-995%

(1R)-1-(2,5-Dimethoxyphenyl)ethan-1-ol

739.0/50mg

Detail

A1122263156713-10-995%

(1S)-1-(2,5-Dimethoxyphenyl)ethan-1-ol

739.0/50mg

Detail