Regio- and stereoselective 1(S)-camphorsulfonylation of monoalkoxycalix[4]arenes
摘要:
The reaction of calix[4]arene monoalkyl ethers with 1(S)-camphor-10-sulfonyl chloride yields 1,2- or 1,3-alkoxy-1(S)-camphorsulfonyloxycalixarenes depending on the nature of the base used. In the presence of triethylamine only 1,3-substituted derivatives are formed. Two diastereomers of the 1,2-substituted calixarenes with clockwise and anticlockwise arrangement of alkyl and camphorsulfonyl groups at the narrow rim are formed in the presence of sodium hydride or potassium carbonate. Due to chiral induction of the camphorsulfonyl group the 1,2-substitution is diastereoselective. The ratio of diastereomers formed is dependent on the alkyl groups at the calixarene narrow rim. (C) 2008 Published by Elsevier Ltd.
DEVICES AND METHODS INCLUDING A PRECONCENTRATOR MATERIAL FOR DETECTION OF ANALYTES
申请人:MASSACHUSETTS INSTITUTE OF TECHNOLOGY
公开号:US20160231267A1
公开(公告)日:2016-08-11
Embodiments described herein provide devices and methods for the determination of analytes. The device typically includes an absorbent material that allows for an analyte sample to be concentrated and analyzed simultaneously and within a short period of time (e.g., less than 10 seconds). Embodiments described herein can provide portable and easily operable devices for on-site, real time field monitoring with high sensitivity, selectivity, and fast response time.
A method for the first general and highyieldsynthesis of calix[4]arene monoalkyl ethers (4) has been developed by treating the easily available -(2) or dialkyl ethers (3) with the equivalent amount of iodotrymethylsilane in CHCl3.
The reaction of calix[4]arene monoalkyl ethers with 1(S)-camphor-10-sulfonyl chloride yields 1,2- or 1,3-alkoxy-1(S)-camphorsulfonyloxycalixarenes depending on the nature of the base used. In the presence of triethylamine only 1,3-substituted derivatives are formed. Two diastereomers of the 1,2-substituted calixarenes with clockwise and anticlockwise arrangement of alkyl and camphorsulfonyl groups at the narrow rim are formed in the presence of sodium hydride or potassium carbonate. Due to chiral induction of the camphorsulfonyl group the 1,2-substitution is diastereoselective. The ratio of diastereomers formed is dependent on the alkyl groups at the calixarene narrow rim. (C) 2008 Published by Elsevier Ltd.