Bridging of resorcin[4]arenes in the chair conformation to cavitands having two pairs of axial and equatorial substituents

O. Middel; Willem Verboom; A.J.R.L. Hulst; Huub Kooijman; Anthony L. Spek; David Reinhoudt

doi:10.1021/jo9810258

Bridging of resorcin[4]arenes in the chair conformation to cavitands having two pairs of axial and equatorial substituents

O. Middel, Willem Verboom, A.J.R.L. Hulst, Huub Kooijman, Anthony L. Spek, David Reinhoudt

Research output: Contribution to journal › Article › Academic › peer-review

17 Citations (Scopus)

3 Downloads (Pure)

Abstract

3-7 with bromochloromethane. According to X-ray analysis of cavitand 19 and 1-D and 2-D NMR spectroscopy for 18, the cavitands possess a stereochemistry with two adjacent aryl substituents in the axial position and the two others in the equatorial position. The starting methylresorcin-[4]arenes 3-7 were obtained exclusively in the chair conformation in 30-98% yield upon condensation of 2-methylresorcinol with aryl aldehydes.

Original language	Undefined
Pages (from-to)	8259-8265
Journal	The journal of organic chemistry
Volume	63
Issue number	63
DOIs	https://doi.org/10.1021/jo9810258
Publication status	Published - 1998

Keywords

METIS-105977
IR-11066

Access to Document

10.1021/jo9810258

Cite this

@article{0b9387c5ff544abdb4c318e1282391c6,

title = "Bridging of resorcin[4]arenes in the chair conformation to cavitands having two pairs of axial and equatorial substituents",

abstract = "3-7 with bromochloromethane. According to X-ray analysis of cavitand 19 and 1-D and 2-D NMR spectroscopy for 18, the cavitands possess a stereochemistry with two adjacent aryl substituents in the axial position and the two others in the equatorial position. The starting methylresorcin-[4]arenes 3-7 were obtained exclusively in the chair conformation in 30-98% yield upon condensation of 2-methylresorcinol with aryl aldehydes.",

keywords = "METIS-105977, IR-11066",

author = "O. Middel and Willem Verboom and A.J.R.L. Hulst and Huub Kooijman and Spek, {Anthony L.} and David Reinhoudt",

year = "1998",

doi = "10.1021/jo9810258",

language = "Undefined",

volume = "63",

pages = "8259--8265",

journal = "The journal of organic chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "63",

}

TY - JOUR

T1 - Bridging of resorcin[4]arenes in the chair conformation to cavitands having two pairs of axial and equatorial substituents

AU - Middel, O.

AU - Verboom, Willem

AU - Hulst, A.J.R.L.

AU - Kooijman, Huub

AU - Spek, Anthony L.

AU - Reinhoudt, David

PY - 1998

Y1 - 1998

N2 - 3-7 with bromochloromethane. According to X-ray analysis of cavitand 19 and 1-D and 2-D NMR spectroscopy for 18, the cavitands possess a stereochemistry with two adjacent aryl substituents in the axial position and the two others in the equatorial position. The starting methylresorcin-[4]arenes 3-7 were obtained exclusively in the chair conformation in 30-98% yield upon condensation of 2-methylresorcinol with aryl aldehydes.

AB - 3-7 with bromochloromethane. According to X-ray analysis of cavitand 19 and 1-D and 2-D NMR spectroscopy for 18, the cavitands possess a stereochemistry with two adjacent aryl substituents in the axial position and the two others in the equatorial position. The starting methylresorcin-[4]arenes 3-7 were obtained exclusively in the chair conformation in 30-98% yield upon condensation of 2-methylresorcinol with aryl aldehydes.

KW - METIS-105977

KW - IR-11066

U2 - 10.1021/jo9810258

DO - 10.1021/jo9810258

M3 - Article

SN - 0022-3263

VL - 63

SP - 8259

EP - 8265

JO - The journal of organic chemistry

JF - The journal of organic chemistry

IS - 63

ER -