Synthesis of dialkylamines via the reaction of organoboranes with n-chloroalkylamines

Journal Article · Fri May 04 04:00:00 EDT 1984 · J. Org. Chem.; (United States)

DOI:https://doi.org/10.1021/jo00183a035· OSTI ID:6550048

Kabalka, G W; McCollum, G W; Kunda, S A

The reaction of trialkylboranes with n-chloroalkylamines to produce a wide variety of functionally substituted dialkylamines in good yield is reported. The reaction is presumed to occur via an anionotropic migration of an alkyl group from boron to nitrogen. The possibility of a competitive free-radical reaction occurring is evidenced by the formation of alkyl chlorides as byproducts. Results of syntheses by this method are presented in one table, and data documenting the competitive free-radical reaction is contained in a second table.

• Research Organization: Univ. of Tennessee, Knoxville
• DOE Contract Number: AS05-80EV10363
• OSTI ID: 6550048
• Journal Information: J. Org. Chem.; (United States), Journal Name: J. Org. Chem.; (United States) Vol. 49:9; ISSN JOCEA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
AMINES
BORANES
BORON COMPOUNDS
CHEMICAL REACTION KINETICS
CHEMICAL REACTIONS
CHLORINATED ALICYCLIC HYDROCARBONS
DATA
EXPERIMENTAL DATA
HALOGENATED ALICYCLIC HYDROCARBONS
INFORMATION
KINETICS
NUMERICAL DATA
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANOMETALLIC COMPOUNDS
REACTION KINETICS
SYNTHESIS