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Synthesis 2008(20): 3219-3222  
DOI: 10.1055/s-0028-1083145
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Facile Synthesis of Bicyclo Orthoesters and Bicyclo Amide Acetals Using α,α-Difluoroalkylamines

Seiko Tange, Tsuyoshi Fukuhara, Shoji Hara*
Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan
Fax: +81(11)7066556; e-Mail: shara@eng.hokudai.ac.jp;
Further Information

Publication History

Received 23 May 2008
Publication Date:
25 September 2008 (online)

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Abstract

Bicyclo orthoesters and amide acetals were prepared from the corresponding triols or diethanolamines using α,α-difluoroalkylamines. The reaction proceeded under milder conditions than conventional methods. 4-tert-Butyl-1-(4-ethynylphenyl)tri­oxabicyclo[2.2.2]octane, a new class of insecticide, was prepared from a triol in three steps using a difluoroalkylamine.

Key words

bicyclo orthoesters - bicyclo amide acetals - α,α-difluoroalkylamines - protecting groups - polymers