Ritter-type reactions of N-chlorosaccharin: A method for the electrophilic diamination of alkenes

Kevin I. Booker-Milburn; Dominic J. Guly; Brian Cox; Panayiotis A. Procopiou

doi:10.1021/ol035374m

Ritter-type reactions of N-chlorosaccharin: A method for the electrophilic diamination of alkenes

Kevin I. Booker-Milburn^*, Dominic J. Guly, Brian Cox, Panayiotis A. Procopiou

^*Corresponding author for this work

Research output: Contribution to journal › Article (Academic Journal) › peer-review

59 Citations (Scopus)

Abstract

(Matrix presented) N-Chlorosaccharin has been shown to undergo electrophilic Ritter-type reactions with alkenes in acetonitrile. The resulting labile β-chloro sulfonylamidines can be ring-opened and cyclized to imidazolines. Overall this provides a one pot method for the electrophilic diamination of alkenes. Competing aziridine formation as well as allylic chlorination are also observed depending on the nature of the alkene used.

Translated title of the contribution	Ritter Type Reactions of N-Chlorosaccharin: A Method for the Electrophilic Diamination of Alkenes
Original language	English
Pages (from-to)	3313-3315
Number of pages	3
Journal	Organic Letters
Volume	5
Issue number	18
DOIs	https://doi.org/10.1021/ol035374m
Publication status	Published - 4 Sep 2003

Bibliographical note

Publisher: Am. Chem. Soc

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10.1021/ol035374m

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title = "Ritter-type reactions of N-chlorosaccharin: A method for the electrophilic diamination of alkenes",

abstract = "(Matrix presented) N-Chlorosaccharin has been shown to undergo electrophilic Ritter-type reactions with alkenes in acetonitrile. The resulting labile β-chloro sulfonylamidines can be ring-opened and cyclized to imidazolines. Overall this provides a one pot method for the electrophilic diamination of alkenes. Competing aziridine formation as well as allylic chlorination are also observed depending on the nature of the alkene used.",

author = "Booker-Milburn, {Kevin I.} and Guly, {Dominic J.} and Brian Cox and Procopiou, {Panayiotis A.}",

note = "Publisher: Am. Chem. Soc",

year = "2003",

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doi = "10.1021/ol035374m",

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volume = "5",

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TY - JOUR

T1 - Ritter-type reactions of N-chlorosaccharin

T2 - A method for the electrophilic diamination of alkenes

AU - Booker-Milburn, Kevin I.

AU - Guly, Dominic J.

AU - Cox, Brian

AU - Procopiou, Panayiotis A.

N1 - Publisher: Am. Chem. Soc

PY - 2003/9/4

Y1 - 2003/9/4

N2 - (Matrix presented) N-Chlorosaccharin has been shown to undergo electrophilic Ritter-type reactions with alkenes in acetonitrile. The resulting labile β-chloro sulfonylamidines can be ring-opened and cyclized to imidazolines. Overall this provides a one pot method for the electrophilic diamination of alkenes. Competing aziridine formation as well as allylic chlorination are also observed depending on the nature of the alkene used.

AB - (Matrix presented) N-Chlorosaccharin has been shown to undergo electrophilic Ritter-type reactions with alkenes in acetonitrile. The resulting labile β-chloro sulfonylamidines can be ring-opened and cyclized to imidazolines. Overall this provides a one pot method for the electrophilic diamination of alkenes. Competing aziridine formation as well as allylic chlorination are also observed depending on the nature of the alkene used.

UR - http://www.scopus.com/inward/record.url?scp=0141744636&partnerID=8YFLogxK

U2 - 10.1021/ol035374m

DO - 10.1021/ol035374m

M3 - Article (Academic Journal)

C2 - 12943415

VL - 5

SP - 3313

EP - 3315

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 18

ER -