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^*

^*Corresponding author for this work

Institute of Chemistry

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

13 Scopus citations

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

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© 2018 American Chemical Society.

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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.",

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

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