DOI: 10.1246/cl.1992.1095. On the Origin of the Distal vs. Proximal Regioselectivity in Di-<i>O</i>-alkylation of Calix[4]arenes

On the Origin of the Distal vs. Proximal Regioselectivity in Di-O-alkylation of Calix[4]arenes

10.1246/cl.1992.1095

Crossref journal-article

Oxford University Press (OUP)

Chemistry Letters (286)

Abstract

Abstract The mechanistic basis of the distal vs. proximal regioselectivity in di-O-alkylation of calix[4]arene was investigated through the detailed product analyses. It was found that (i) the regioselectivity is profoundly affected by the residual intramolecular hydrogen-bonds and (ii) the distal isomer is more reactive for further O-alkylation than the proximal isomer, resulting in the “apparent” proximal selectivity.

Bibliography

Araki, K., Iwamoto, K., Shigematsu, S., & Shinkai, S. (1992). On the Origin of the Distal vs. Proximal Regioselectivity in Di-O-alkylation of Calix[4]arenes. Chemistry Letters, 21(6), 1095â1098.

Authors 4

Koji Araki (first)
Koji Iwamoto (additional)
Satoshi Shigematsu (additional)
Seiji Shinkai (additional)

References 9 Referenced 16

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10.1021/jo00016a027
10.1016/S0040-4039(00)97270-8
10.1016/S0040-4039(00)92097-5
10.1021/jo00015a039
10.1016/S0040-4039(00)78816-2
10.1021/jo00284a001
{'key': '2024011823521405000_r8'}
{'key': '2024011823521405000_r9'}

Dates

Type	When
Created	19 years, 3 months ago (May 1, 2006, 11:06 p.m.)
Deposited	1 year, 7 months ago (Jan. 18, 2024, 1:52 p.m.)
Indexed	1 year ago (Aug. 12, 2024, 7:45 p.m.)
Issued	33 years, 2 months ago (June 1, 1992)
Published	33 years, 2 months ago (June 1, 1992)
Published Online	19 years, 3 months ago (May 2, 2006)
Published Print	33 years, 2 months ago (June 1, 1992)

Funders 0

None

BibTeX

@article{Araki_1992, title={On the Origin of the Distal vs. Proximal Regioselectivity in Di-O-alkylation of Calix[4]arenes}, volume={21}, ISSN={1348-0715}, url={http://dx.doi.org/10.1246/cl.1992.1095}, DOI={10.1246/cl.1992.1095}, number={6}, journal={Chemistry Letters}, publisher={Oxford University Press (OUP)}, author={Araki, Koji and Iwamoto, Koji and Shigematsu, Satoshi and Shinkai, Seiji}, year={1992}, month=jun, pages={1095–1098} }

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