The influence of reaction conditions on the Diels-Alder cycloadditions of 2-thio-3-chloroacrylamides; Investigation of thermal, catalytic and microwave conditions

Marie Kissane; Denis Lynch; Jay Chopra; Simon E. Lawrence; Anita R. Maguire

doi:10.1039/c0ob00368a

The influence of reaction conditions on the Diels-Alder cycloadditions of 2-thio-3-chloroacrylamides; Investigation of thermal, catalytic and microwave conditions

Marie Kissane
, Denis Lynch
, Jay Chopra
, Simon E. Lawrence
, Anita R. Maguire

University College Cork

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

Abstract

The Diels-Alder cycloadditions of cyclopentadiene and 2,3-dimethyl-1,3- butadiene to a range of 2-thio-3-chloroacrylamides under thermal, catalytic and microwave conditions is described. The influence of reaction conditions on the outcome of the cycloadditions, in particular the stereoselectivity and reaction efficiency, is discussed. While the cycloadditions have been attempted at the sulfide, sulfoxide and sulfone levels of oxidation, use of the sulfoxide derivatives is clearly beneficial for stereoselective construction of Diels-Alder cycloadducts.

Original language	English
Pages (from-to)	5602-5613
Number of pages	12
Journal	Organic and Biomolecular Chemistry
Volume	8
Issue number	24
DOIs	https://doi.org/10.1039/c0ob00368a
Publication status	Published - 21 Dec 2010

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https://hdl.handle.net/10468/594Licence: CC BY-NC-ND

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title = "The influence of reaction conditions on the Diels-Alder cycloadditions of 2-thio-3-chloroacrylamides; Investigation of thermal, catalytic and microwave conditions",

abstract = "The Diels-Alder cycloadditions of cyclopentadiene and 2,3-dimethyl-1,3- butadiene to a range of 2-thio-3-chloroacrylamides under thermal, catalytic and microwave conditions is described. The influence of reaction conditions on the outcome of the cycloadditions, in particular the stereoselectivity and reaction efficiency, is discussed. While the cycloadditions have been attempted at the sulfide, sulfoxide and sulfone levels of oxidation, use of the sulfoxide derivatives is clearly beneficial for stereoselective construction of Diels-Alder cycloadducts.",

author = "Marie Kissane and Denis Lynch and Jay Chopra and Lawrence, \{Simon E.\} and Maguire, \{Anita R.\}",

year = "2010",

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T1 - The influence of reaction conditions on the Diels-Alder cycloadditions of 2-thio-3-chloroacrylamides; Investigation of thermal, catalytic and microwave conditions

AU - Kissane, Marie

AU - Lynch, Denis

AU - Chopra, Jay

AU - Lawrence, Simon E.

AU - Maguire, Anita R.

PY - 2010/12/21

Y1 - 2010/12/21

N2 - The Diels-Alder cycloadditions of cyclopentadiene and 2,3-dimethyl-1,3- butadiene to a range of 2-thio-3-chloroacrylamides under thermal, catalytic and microwave conditions is described. The influence of reaction conditions on the outcome of the cycloadditions, in particular the stereoselectivity and reaction efficiency, is discussed. While the cycloadditions have been attempted at the sulfide, sulfoxide and sulfone levels of oxidation, use of the sulfoxide derivatives is clearly beneficial for stereoselective construction of Diels-Alder cycloadducts.

AB - The Diels-Alder cycloadditions of cyclopentadiene and 2,3-dimethyl-1,3- butadiene to a range of 2-thio-3-chloroacrylamides under thermal, catalytic and microwave conditions is described. The influence of reaction conditions on the outcome of the cycloadditions, in particular the stereoselectivity and reaction efficiency, is discussed. While the cycloadditions have been attempted at the sulfide, sulfoxide and sulfone levels of oxidation, use of the sulfoxide derivatives is clearly beneficial for stereoselective construction of Diels-Alder cycloadducts.

UR - https://www.scopus.com/pages/publications/78649500519

U2 - 10.1039/c0ob00368a

DO - 10.1039/c0ob00368a

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SN - 1477-0520

VL - 8

SP - 5602

EP - 5613

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 24

ER -

The influence of reaction conditions on the Diels-Alder cycloadditions of 2-thio-3-chloroacrylamides; Investigation of thermal, catalytic and microwave conditions

Abstract

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