Tetrahedron letters

A convenient conversion of primary amines into the corresponding halides—Radical promoted halodeamination via N-substituted-N-Tosylhydrazines

LR Collazo, FS Guziec, WX Hu, R Pankayatselvan

Index: Collazo, Luis R.; Guziec, Frank S.; Hu, Wei-Xiao Jr.; Pankayatselvan, Ratnadevi Tetrahedron Letters, 1994 , vol. 35, # 43 p. 7911 - 7914

Full Text: HTML

Citation Number: 7

Abstract

Abstract Treatment of 1-substituted-1-tosylhydrazines with 2 equivalents of NCS or NBS in dry THF in presence of light affords the corresponding alkyl halides in good yields. This reaction presumably involves the initial formation of a stabilized hydrazyl radical which is halogenated in a radical chain process. Elimination of p-toluenesulfinic acid and extrusion of nitrogen leads to the corresponding alkyl halide. This route provides an improved method ...

Related Articles:

Betylates. 3. Preparative nucleophilic substitution by way of [2]-,[3]-, and [4] betylates. Stoichiometric phase transfer and substrate-reagent ion-pair (SRIP) reactions of …

[King,J.F.; Loosmore,S.M.; Aslam,M. Journal of the American Chemical Society, 1982 , vol. 104, p. 7108]

Betylates. 3. Preparative nucleophilic substitution by way of [2]-,[3]-, and [4] betylates. Stoichiometric phase transfer and substrate-reagent ion-pair (SRIP) reactions of …

[King,J.F.; Loosmore,S.M.; Aslam,M. Journal of the American Chemical Society, 1982 , vol. 104, p. 7108]

Preparation of alkyl chlorides, acid chlorides, and amides using polymer-supported phosphines and carbon tetrachloride: mechanism of these reactions

[Harrison, Charles R.; Hodge, Philip; Hunt, Barry J.; Khoshdel, Ezzatollah; Richardson, Graham Journal of Organic Chemistry, 1983 , vol. 48, # 21 p. 3721 - 3728]

Pivaloyl chloride/DMF: a new reagent for conversion of alcohols to chlorides

[Dubey, Abhishek; Upadhyay, Arun K.; Kumar, Pradeep Tetrahedron Letters, 2010 , vol. 51, # 4 p. 744 - 746]

A Safe and Efficient Procedure to Prepare Alkyl and Alkoxyalkyl Chlorides and Dichlorides by Catalytic Decomposition of the Corresponding Alkyl and Alkoxyalkyl …

[Violleau; Thiebaud; Borredon; Le Gars Synthetic Communications, 2001 , vol. 31, # 3 p. 367 - 373]

More Articles...