Mechanistic study on the oxidative coupling of amines to imines on K-10 montmorillonite

Valentina Atanassova; Kristen Ganno; Aditya Kulkarni; Shainaz M. Landge; Steven Curtis; Michelle Foster; Béla Török

doi:10.1016/j.clay.2010.12.034

Mechanistic study on the oxidative coupling of amines to imines on K-10 montmorillonite

Valentina Atanassova
, Kristen Ganno
, Aditya Kulkarni
, Shainaz M. Landge
, Steven Curtis
, Michelle Foster
, Béla Török

Chemistry

University of Massachusetts Boston

Research output: Contribution to journal › Article › peer-review

Abstract

A mechanistic study of the K-10 montmorillonite-catalyzed microwave-assisted oxidative self-coupling of benzylamine and cross coupling of benzylamines with anilines and aliphatic amines is described. The coupling of benzylamines readily produced benzylidene benzylamines, while reactions of benzylamine with aliphatic amines and anilines resulted in benzylidene alkylamines and benzylidene anilines. The mechanism of the reaction has been investigated by varying reaction conditions, kinetic studies, thermogravimetric analysis and DRIFT spectroscopy. The data obtained clarified the steps of this multistep reaction sequence and a mechanistic scheme has been proposed.

Original language	English
Pages (from-to)	220-226
Number of pages	7
Journal	Applied Clay Science
Volume	53
Issue number	2
DOIs	https://doi.org/10.1016/j.clay.2010.12.034
State	Published - Aug 2011

ASJC Scopus Subject Areas

Geology
Geochemistry and Petrology

Keywords

Benzylamine
DRIFT spectroscopy
K-10 montmorillonite
Oxidative coupling
Thermogravimetry

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10.1016/j.clay.2010.12.034

Cite this

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title = "Mechanistic study on the oxidative coupling of amines to imines on K-10 montmorillonite",

abstract = "A mechanistic study of the K-10 montmorillonite-catalyzed microwave-assisted oxidative self-coupling of benzylamine and cross coupling of benzylamines with anilines and aliphatic amines is described. The coupling of benzylamines readily produced benzylidene benzylamines, while reactions of benzylamine with aliphatic amines and anilines resulted in benzylidene alkylamines and benzylidene anilines. The mechanism of the reaction has been investigated by varying reaction conditions, kinetic studies, thermogravimetric analysis and DRIFT spectroscopy. The data obtained clarified the steps of this multistep reaction sequence and a mechanistic scheme has been proposed.",

keywords = "Benzylamine, DRIFT spectroscopy, K-10 montmorillonite, Oxidative coupling, Thermogravimetry",

author = "Valentina Atanassova and Kristen Ganno and Aditya Kulkarni and Landge, \{Shainaz M.\} and Steven Curtis and Michelle Foster and B{\'e}la T{\"o}r{\"o}k",

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language = "English",

volume = "53",

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publisher = "Elsevier B.V.",

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TY - JOUR

T1 - Mechanistic study on the oxidative coupling of amines to imines on K-10 montmorillonite

AU - Atanassova, Valentina

AU - Ganno, Kristen

AU - Kulkarni, Aditya

AU - Landge, Shainaz M.

AU - Curtis, Steven

AU - Foster, Michelle

AU - Török, Béla

PY - 2011/8

Y1 - 2011/8

N2 - A mechanistic study of the K-10 montmorillonite-catalyzed microwave-assisted oxidative self-coupling of benzylamine and cross coupling of benzylamines with anilines and aliphatic amines is described. The coupling of benzylamines readily produced benzylidene benzylamines, while reactions of benzylamine with aliphatic amines and anilines resulted in benzylidene alkylamines and benzylidene anilines. The mechanism of the reaction has been investigated by varying reaction conditions, kinetic studies, thermogravimetric analysis and DRIFT spectroscopy. The data obtained clarified the steps of this multistep reaction sequence and a mechanistic scheme has been proposed.

AB - A mechanistic study of the K-10 montmorillonite-catalyzed microwave-assisted oxidative self-coupling of benzylamine and cross coupling of benzylamines with anilines and aliphatic amines is described. The coupling of benzylamines readily produced benzylidene benzylamines, while reactions of benzylamine with aliphatic amines and anilines resulted in benzylidene alkylamines and benzylidene anilines. The mechanism of the reaction has been investigated by varying reaction conditions, kinetic studies, thermogravimetric analysis and DRIFT spectroscopy. The data obtained clarified the steps of this multistep reaction sequence and a mechanistic scheme has been proposed.

KW - Benzylamine

KW - DRIFT spectroscopy

KW - K-10 montmorillonite

KW - Oxidative coupling

KW - Thermogravimetry

UR - https://www.scopus.com/pages/publications/79960833890

UR - https://www.scopus.com/pages/publications/79960833890#tab=citedBy

U2 - 10.1016/j.clay.2010.12.034

DO - 10.1016/j.clay.2010.12.034

M3 - Article

AN - SCOPUS:79960833890

SN - 0169-1317

VL - 53

SP - 220

EP - 226

JO - Applied Clay Science

JF - Applied Clay Science

IS - 2

ER -

Mechanistic study on the oxidative coupling of amines to imines on K-10 montmorillonite

Abstract

ASJC Scopus Subject Areas

Keywords

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