C-Me Bond Formation at All Methylene Bridges of the Calix[4]arene Scaffold

Ori Shalev; Silvio E. Biali

doi:10.1021/acs.orglett.8b01314

C-Me Bond Formation at All Methylene Bridges of the Calix[4]arene Scaffold

Ori Shalev, Silvio E. Biali

Institute of Chemistry

The Hebrew University of Jerusalem

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

Abstract

A reaction of a distal dibromo diketocalix[4]arene with excess MeLi, followed by acid-catalyzed dehydration, yields a derivative with a pair of opposite exocyclic double bonds, and a pair of trans methyl groups at the bridges. A reaction of a tetrabromo calix[4]arene derivative with excess MeLi yields a calix[4]arene derivative with all methylene bridges monomethylated in all-cis fashion.

Original language	English
Pages (from-to)	3390-3393
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	11
DOIs	https://doi.org/10.1021/acs.orglett.8b01314
State	Published - 1 Jun 2018

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "C-Me Bond Formation at All Methylene Bridges of the Calix[4]arene Scaffold",

abstract = "A reaction of a distal dibromo diketocalix[4]arene with excess MeLi, followed by acid-catalyzed dehydration, yields a derivative with a pair of opposite exocyclic double bonds, and a pair of trans methyl groups at the bridges. A reaction of a tetrabromo calix[4]arene derivative with excess MeLi yields a calix[4]arene derivative with all methylene bridges monomethylated in all-cis fashion.",

author = "Ori Shalev and Biali, \{Silvio E.\}",

note = "Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

year = "2018",

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doi = "10.1021/acs.orglett.8b01314",

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N2 - A reaction of a distal dibromo diketocalix[4]arene with excess MeLi, followed by acid-catalyzed dehydration, yields a derivative with a pair of opposite exocyclic double bonds, and a pair of trans methyl groups at the bridges. A reaction of a tetrabromo calix[4]arene derivative with excess MeLi yields a calix[4]arene derivative with all methylene bridges monomethylated in all-cis fashion.

AB - A reaction of a distal dibromo diketocalix[4]arene with excess MeLi, followed by acid-catalyzed dehydration, yields a derivative with a pair of opposite exocyclic double bonds, and a pair of trans methyl groups at the bridges. A reaction of a tetrabromo calix[4]arene derivative with excess MeLi yields a calix[4]arene derivative with all methylene bridges monomethylated in all-cis fashion.

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U2 - 10.1021/acs.orglett.8b01314

DO - 10.1021/acs.orglett.8b01314

M3 - مقالة

C2 - 29790764

SN - 1523-7060

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SP - 3390

EP - 3393

JO - Organic Letters

JF - Organic Letters

IS - 11

ER -

C-Me Bond Formation at All Methylene Bridges of the Calix[4]arene Scaffold

Abstract

All Science Journal Classification (ASJC) codes

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