Reversible aryl migrations in metallated ureas: Controlled inversion of configuration at a quaternary carbon atom

Daniel J. Tetlow; Mark A. Vincent; Ian H. Hillier; Jonathan Clayden

doi:10.1039/c2cc38704b

Reversible aryl migrations in metallated ureas: Controlled inversion of configuration at a quaternary carbon atom

Daniel J. Tetlow, Mark A. Vincent, Ian H. Hillier, Jonathan Clayden^*

^*Corresponding author for this work

School of Chemistry

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

14 Citations (Scopus)

Abstract

Deprotonation with strong bases of N-vinyl ureas carrying an N′-aryl substituent leads to migration of the N′-aryl group from N to C via an allyllithium; with weaker bases and electron-deficient aryl rings the direction of the migration reverses, and aryl substituents α to the urea N atom may migrate from C to N.

Original language	English
Pages (from-to)	1548-1550
Number of pages	3
Journal	Chemical Communications
Volume	49
Issue number	15
Early online date	3 Jan 2013
DOIs	https://doi.org/10.1039/c2cc38704b
Publication status	Published - 21 Feb 2013

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title = "Reversible aryl migrations in metallated ureas: Controlled inversion of configuration at a quaternary carbon atom",

abstract = "Deprotonation with strong bases of N-vinyl ureas carrying an N′-aryl substituent leads to migration of the N′-aryl group from N to C via an allyllithium; with weaker bases and electron-deficient aryl rings the direction of the migration reverses, and aryl substituents α to the urea N atom may migrate from C to N.",

author = "Tetlow, {Daniel J.} and Vincent, {Mark A.} and Hillier, {Ian H.} and Jonathan Clayden",

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T1 - Reversible aryl migrations in metallated ureas

T2 - Controlled inversion of configuration at a quaternary carbon atom

AU - Tetlow, Daniel J.

AU - Vincent, Mark A.

AU - Hillier, Ian H.

AU - Clayden, Jonathan

PY - 2013/2/21

Y1 - 2013/2/21

N2 - Deprotonation with strong bases of N-vinyl ureas carrying an N′-aryl substituent leads to migration of the N′-aryl group from N to C via an allyllithium; with weaker bases and electron-deficient aryl rings the direction of the migration reverses, and aryl substituents α to the urea N atom may migrate from C to N.

AB - Deprotonation with strong bases of N-vinyl ureas carrying an N′-aryl substituent leads to migration of the N′-aryl group from N to C via an allyllithium; with weaker bases and electron-deficient aryl rings the direction of the migration reverses, and aryl substituents α to the urea N atom may migrate from C to N.

UR - http://www.scopus.com/inward/record.url?scp=84873035393&partnerID=8YFLogxK

U2 - 10.1039/c2cc38704b

DO - 10.1039/c2cc38704b

M3 - Article (Academic Journal)

C2 - 23324729

AN - SCOPUS:84873035393

SN - 1359-7345

VL - 49

SP - 1548

EP - 1550

JO - Chemical Communications

JF - Chemical Communications

IS - 15

ER -

Reversible aryl migrations in metallated ureas: Controlled inversion of configuration at a quaternary carbon atom

Abstract

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