Aziridines, 61 [1]: Ring Opening of 2,2-Dimethyl-1-sulfonylaziridines by Anilines: Regioselectivity and Revised Structure of Main Products

Berthold Buchholz Buchholz; Andreas Onistschenko Onistschenko; Helmut Stamm Stamm; Pen Yuan Lin

doi:10.1515/znb-1993-0414

Aziridines, 61 [1]: Ring Opening of 2,2-Dimethyl-1-sulfonylaziridines by Anilines: Regioselectivity and Revised Structure of Main Products

Berthold Buchholz Buchholz
, Andreas Onistschenko Onistschenko
, Helmut Stamm Stamm
, Pen Yuan Lin

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

Abstract

It is shown (1) that in most reactions of anilines 2 with 1-sulfonyl-2,2-dim ethylaziridines 1 both isomeric products 3 and 4 are formed, (2) that the “normal” product 4 obtained by attack on position 3 of 1 usually arises in a small or negligible amount that seems to decrease with decreasing basicity of 2, and (3) that the amount of 4 strongly increases w ith increasing steric demand of 2. Formation of 4 is explained by a lag of bond making in SN2.

Original language	English
Pages (from-to)	483-487
Number of pages	5
Journal	Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences
Volume	48
Issue number	4
DOIs	https://doi.org/10.1515/znb-1993-0414
Publication status	Published - Apr 1 1993
Externally published	Yes

Keywords

1-Sulfonyl-2,2-dim ethylaziridines
Basicity Effect
N-Aryl-N′-sulfonyl-gem-dimethylethylenediamines
Regioselectivity of Nucleophilic Ring Opening
Steric Hindrance Effect

ASJC Scopus subject areas

General Chemistry

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10.1515/znb-1993-0414

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Aziridines, 61 [1]: Ring Opening of 2,2-Dimethyl-1-sulfonylaziridines by Anilines: Regioselectivity and Revised Structure of Main Products. / Buchholz, Berthold Buchholz; Onistschenko, Andreas Onistschenko; Stamm, Helmut Stamm et al.
In: Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, Vol. 48, No. 4, 01.04.1993, p. 483-487.

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

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abstract = "It is shown (1) that in most reactions of anilines 2 with 1-sulfonyl-2,2-dim ethylaziridines 1 both isomeric products 3 and 4 are formed, (2) that the “normal” product 4 obtained by attack on position 3 of 1 usually arises in a small or negligible amount that seems to decrease with decreasing basicity of 2, and (3) that the amount of 4 strongly increases w ith increasing steric demand of 2. Formation of 4 is explained by a lag of bond making in SN2.",

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AU - Buchholz, Berthold Buchholz

AU - Onistschenko, Andreas Onistschenko

AU - Stamm, Helmut Stamm

AU - Lin, Pen Yuan

PY - 1993/4/1

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N2 - It is shown (1) that in most reactions of anilines 2 with 1-sulfonyl-2,2-dim ethylaziridines 1 both isomeric products 3 and 4 are formed, (2) that the “normal” product 4 obtained by attack on position 3 of 1 usually arises in a small or negligible amount that seems to decrease with decreasing basicity of 2, and (3) that the amount of 4 strongly increases w ith increasing steric demand of 2. Formation of 4 is explained by a lag of bond making in SN2.

AB - It is shown (1) that in most reactions of anilines 2 with 1-sulfonyl-2,2-dim ethylaziridines 1 both isomeric products 3 and 4 are formed, (2) that the “normal” product 4 obtained by attack on position 3 of 1 usually arises in a small or negligible amount that seems to decrease with decreasing basicity of 2, and (3) that the amount of 4 strongly increases w ith increasing steric demand of 2. Formation of 4 is explained by a lag of bond making in SN2.

KW - 1-Sulfonyl-2,2-dim ethylaziridines

KW - Basicity Effect

KW - N-Aryl-N′-sulfonyl-gem-dimethylethylenediamines

KW - Regioselectivity of Nucleophilic Ring Opening

KW - Steric Hindrance Effect

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Aziridines, 61 [1]: Ring Opening of 2,2-Dimethyl-1-sulfonylaziridines by Anilines: Regioselectivity and Revised Structure of Main Products

Abstract

Keywords

ASJC Scopus subject areas

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