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 journalArticle

1 Citation (Scopus)

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 languageEnglish
Pages (from-to)483-487
Number of pages5
JournalZeitschrift fur Naturforschung - Section B Journal of Chemical Sciences
Volume48
Issue number4
DOIs
Publication statusPublished - Apr 1 1993
Externally publishedYes

Fingerprint

Aniline Compounds
Aziridines
Regioselectivity
Alkalinity

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

  • Chemistry(all)

Cite this

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; Lin, Pen Yuan.

In: Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, Vol. 48, No. 4, 01.04.1993, p. 483-487.

Research output: Contribution to journalArticle

Buchholz, Berthold Buchholz ; Onistschenko, Andreas Onistschenko ; Stamm, Helmut Stamm ; Lin, Pen Yuan. / Aziridines, 61 [1] : Ring Opening of 2,2-Dimethyl-1-sulfonylaziridines by Anilines: Regioselectivity and Revised Structure of Main Products. In: Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences. 1993 ; Vol. 48, No. 4. pp. 483-487.
@article{5d1bd643ecc44e12ade0fd351e58ff39,
title = "Aziridines, 61 [1]: Ring Opening of 2,2-Dimethyl-1-sulfonylaziridines by Anilines: Regioselectivity and Revised Structure of Main Products",
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.",
keywords = "1-Sulfonyl-2,2-dim ethylaziridines, Basicity Effect, N-Aryl-N′-sulfonyl-gem-dimethylethylenediamines, Regioselectivity of Nucleophilic Ring Opening, Steric Hindrance Effect",
author = "Buchholz, {Berthold Buchholz} and Onistschenko, {Andreas Onistschenko} and Stamm, {Helmut Stamm} and Lin, {Pen Yuan}",
year = "1993",
month = "4",
day = "1",
doi = "10.1515/znb-1993-0414",
language = "English",
volume = "48",
pages = "483--487",
journal = "Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences",
issn = "0932-0776",
publisher = "Verlag der Zeitschrift fur Naturforschung",
number = "4",

}

TY - JOUR

T1 - Aziridines, 61 [1]

T2 - Ring Opening of 2,2-Dimethyl-1-sulfonylaziridines by Anilines: Regioselectivity and Revised Structure of Main Products

AU - Buchholz, Berthold Buchholz

AU - Onistschenko, Andreas Onistschenko

AU - Stamm, Helmut Stamm

AU - Lin, Pen Yuan

PY - 1993/4/1

Y1 - 1993/4/1

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

UR - http://www.scopus.com/inward/record.url?scp=84945050582&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84945050582&partnerID=8YFLogxK

U2 - 10.1515/znb-1993-0414

DO - 10.1515/znb-1993-0414

M3 - Article

VL - 48

SP - 483

EP - 487

JO - Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences

JF - Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences

SN - 0932-0776

IS - 4

ER -