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Last of the gem-Difluorocycloalkanes: Synthesis and Characterization of 2,2-Difluorocyclobutyl-Substituted Building Blocks

Last of the gem-Difluorocycloalkanes: Synthesis and Characterization of 2,2-Difluorocyclobutyl-Substituted Building Blocks

Anton V Chernykh, Kostiantyn P Melnykov, Nataliya A Tolmacheva, Ivan S Kondratov, Dmytro S Radchenko, Constantin G Daniliuc, Dmitriy M Volochnyuk, Sergey V Ryabukhin, Yuliya O Kuchkovska, Oleksandr O Grygorenko

J Org Chem. 2019 Jul 5;84(13):8487-8496.

PMID: 30990713

Abstract:

An efficient approach to synthesis of previously unavailable 2-substituted difluorocyclobutane building blocks was developed and applied on a multigram scale. The key step of the synthetic sequence included deoxofluorination of O-protected 2-(hydroxylmethyl)cyclobutanone. Dissociation constants (p Ka) and log P values for 2,2-difluorocyclobutaneamine and 2,2-difluorocyclobutanecarboxylic acid or their derivatives were measured and compared with the values obtained for the corresponding 3,3-difluorocyclobutane derivatives and nonfluorinated counterparts. Three-dimensional structures of 2,2- and 3,3-difluorocyclobutanamines were compared using exit vector plot analysis of X-ray crystallographic data.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AS24722	2-(Tetradecyl-d29)cyclobutanone			Price

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