Achieving conformational control over C-C, C-N and C-O bonds in biaryls, N,N′-diarylureas and diaryl ethers: Advantages of a relay axis

Mark S. Betson; Ann Bracegirdle; Jonathan Clayden; Madeleine Helliwell; Andrew Lund; Mark Pickworth; Timothy J. Snape; Christopher P. Worrall

doi:10.1039/b614618j

Achieving conformational control over C-C, C-N and C-O bonds in biaryls, N,N′-diarylureas and diaryl ethers: Advantages of a relay axis

Mark S. Betson, Ann Bracegirdle, Jonathan Clayden^*, Madeleine Helliwell, Andrew Lund, Mark Pickworth, Timothy J. Snape, Christopher P. Worrall

^*Corresponding author for this work

School of Chemistry

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

22 Citations (Scopus)

Abstract

The orientation of Ar-C, Ar-N and Ar-O bonds in biaryls, N,N′-diarylureas and diaryl ethers (whose conformers are distinguishable by NMR) may be controlled with a selectivity up to >95: 5 by an adjacent stereogenic centre; the selectivity may be greater when a second stereogenic axis is inserted between the controlling centre and the slowly rotating bond.

Original language	English
Pages (from-to)	754-756
Number of pages	3
Journal	Chemical Communications
Issue number	7
Early online date	18 Dec 2006
DOIs	https://doi.org/10.1039/b614618j
Publication status	Published - 21 Feb 2007

Research Groups and Themes

Organic & Biological

Access to Document

10.1039/b614618j

Handle.net

Persistent link

Cite this

@article{02fc9d7dfe9a4144befb1c01063c3ec0,

title = "Achieving conformational control over C-C, C-N and C-O bonds in biaryls, N,N′-diarylureas and diaryl ethers: Advantages of a relay axis",

abstract = "The orientation of Ar-C, Ar-N and Ar-O bonds in biaryls, N,N′-diarylureas and diaryl ethers (whose conformers are distinguishable by NMR) may be controlled with a selectivity up to >95: 5 by an adjacent stereogenic centre; the selectivity may be greater when a second stereogenic axis is inserted between the controlling centre and the slowly rotating bond.",

author = "Betson, \{Mark S.\} and Ann Bracegirdle and Jonathan Clayden and Madeleine Helliwell and Andrew Lund and Mark Pickworth and Snape, \{Timothy J.\} and Worrall, \{Christopher P.\}",

year = "2007",

month = feb,

day = "21",

doi = "10.1039/b614618j",

language = "English",

pages = "754--756",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "7",

}

TY - JOUR

T1 - Achieving conformational control over C-C, C-N and C-O bonds in biaryls, N,N′-diarylureas and diaryl ethers

T2 - Advantages of a relay axis

AU - Betson, Mark S.

AU - Bracegirdle, Ann

AU - Clayden, Jonathan

AU - Helliwell, Madeleine

AU - Lund, Andrew

AU - Pickworth, Mark

AU - Snape, Timothy J.

AU - Worrall, Christopher P.

PY - 2007/2/21

Y1 - 2007/2/21

N2 - The orientation of Ar-C, Ar-N and Ar-O bonds in biaryls, N,N′-diarylureas and diaryl ethers (whose conformers are distinguishable by NMR) may be controlled with a selectivity up to >95: 5 by an adjacent stereogenic centre; the selectivity may be greater when a second stereogenic axis is inserted between the controlling centre and the slowly rotating bond.

AB - The orientation of Ar-C, Ar-N and Ar-O bonds in biaryls, N,N′-diarylureas and diaryl ethers (whose conformers are distinguishable by NMR) may be controlled with a selectivity up to >95: 5 by an adjacent stereogenic centre; the selectivity may be greater when a second stereogenic axis is inserted between the controlling centre and the slowly rotating bond.

UR - https://www.scopus.com/pages/publications/33846932037

U2 - 10.1039/b614618j

DO - 10.1039/b614618j

M3 - Article (Academic Journal)

C2 - 17392973

AN - SCOPUS:33846932037

SN - 1359-7345

SP - 754

EP - 756

JO - Chemical Communications

JF - Chemical Communications

IS - 7

ER -

Achieving conformational control over C-C, C-N and C-O bonds in biaryls, N,N′-diarylureas and diaryl ethers: Advantages of a relay axis

Abstract

Research Groups and Themes

Access to Document

Handle.net

Other files and links

Fingerprint

Cite this