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Conjugate Additions of Secondary Amines and Water to Allenyl Perfluoroalkyl Sulfones

Xiao-Jin Wang

Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

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Yun Lin,

Yun Lin

Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

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Jin-Tao Liu,

Jin-Tao Liu

[email protected]

Project supported by the National Natural Science Foundation of China (No. 20572124).

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Xiao-Jin Wang,

Xiao-Jin Wang

Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

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Yun Lin,

Yun Lin

Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China

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Jin-Tao Liu,

Jin-Tao Liu

[email protected]

Project supported by the National Natural Science Foundation of China (No. 20572124).

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First published: 07 June 2006

https://doi.org/10.1002/cjoc.200690147

Citations: 12

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Abstract

Preparation of allenyl perfluoroalkyl sulfones from perfluoroalkyl sulfinyl chlorides and their reactions with secondary amines and water were studied. At room temperature secondary amines reacted readily with allenyl perfluoroalkyl sulfones to give the corresponding enamine adducts, which underwent rearrangement to afford conjugate enamines in refluxing toluene. Good diastereoslectivities were observed in the addition of diethylamine to γ-ethyl-γ-methylallenyl perfluoroalkyl sulfones. In refluxing acetonitrile, water could also undergo the similar addition with allenyl perfluoroalkyl sulfones.

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Volume24, Issue6

June, 2006

Pages 775-780

Conjugate Additions of Secondary Amines and Water to Allenyl Perfluoroalkyl Sulfones

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Conjugate Additions of Secondary Amines and Water to Allenyl Perfluoroalkyl Sulfones

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