Conversion of phenols into selenophenols: Seleno newman-kwart rearrangement

Anne Sørensen; Brian Rasmussen; Shubham Agarwal; Magnus Schau-Magnussen; Theis I. Sølling; Michael Pittelkow

doi:10.1002/anie.201303773

Conversion of phenols into selenophenols: Seleno newman-kwart rearrangement

Anne Sørensen, Brian Rasmussen, Shubham Agarwal, Magnus Schau-Magnussen, Theis I. Sølling, Michael Pittelkow

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

25 Scopus citations

Abstract

A 'Se'lling point: The first thermally induced O_Ar→Se _Ar migration reaction is reported, and it can be used to prepare aryl selenols in three steps from the corresponding phenols. O-aryl selenocarbamates rearrange to Se-aryl carbamates via a four-membered transition state (see scheme). The aryl selenols (isolated as the diselenides) can be prepared by hydrolysis of the Se-aryl selenocarbamates.

Original language	English
Pages (from-to)	12346-12349
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	52
Issue number	47
DOIs	https://doi.org/10.1002/anie.201303773
State	Published - 18 Nov 2013
Externally published	Yes

Keywords

X-ray crystallography
density functional calculations
kinetics
rearrangement
selenium

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.201303773

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title = "Conversion of phenols into selenophenols: Seleno newman-kwart rearrangement",

abstract = "A 'Se'lling point: The first thermally induced OAr→Se Ar migration reaction is reported, and it can be used to prepare aryl selenols in three steps from the corresponding phenols. O-aryl selenocarbamates rearrange to Se-aryl carbamates via a four-membered transition state (see scheme). The aryl selenols (isolated as the diselenides) can be prepared by hydrolysis of the Se-aryl selenocarbamates.",

keywords = "X-ray crystallography, density functional calculations, kinetics, rearrangement, selenium",

author = "Anne S{\o}rensen and Brian Rasmussen and Shubham Agarwal and Magnus Schau-Magnussen and S{\o}lling, \{Theis I.\} and Michael Pittelkow",

year = "2013",

month = nov,

day = "18",

doi = "10.1002/anie.201303773",

language = "English",

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journal = "Angewandte Chemie - International Edition",

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T1 - Conversion of phenols into selenophenols

T2 - Seleno newman-kwart rearrangement

AU - Sørensen, Anne

AU - Rasmussen, Brian

AU - Agarwal, Shubham

AU - Schau-Magnussen, Magnus

AU - Sølling, Theis I.

AU - Pittelkow, Michael

PY - 2013/11/18

Y1 - 2013/11/18

N2 - A 'Se'lling point: The first thermally induced OAr→Se Ar migration reaction is reported, and it can be used to prepare aryl selenols in three steps from the corresponding phenols. O-aryl selenocarbamates rearrange to Se-aryl carbamates via a four-membered transition state (see scheme). The aryl selenols (isolated as the diselenides) can be prepared by hydrolysis of the Se-aryl selenocarbamates.

AB - A 'Se'lling point: The first thermally induced OAr→Se Ar migration reaction is reported, and it can be used to prepare aryl selenols in three steps from the corresponding phenols. O-aryl selenocarbamates rearrange to Se-aryl carbamates via a four-membered transition state (see scheme). The aryl selenols (isolated as the diselenides) can be prepared by hydrolysis of the Se-aryl selenocarbamates.

KW - X-ray crystallography

KW - density functional calculations

KW - kinetics

KW - rearrangement

KW - selenium

UR - https://www.scopus.com/pages/publications/84887524239

U2 - 10.1002/anie.201303773

DO - 10.1002/anie.201303773

M3 - Article

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AN - SCOPUS:84887524239

SN - 1433-7851

VL - 52

SP - 12346

EP - 12349

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 47

ER -

Conversion of phenols into selenophenols: Seleno newman-kwart rearrangement

Abstract

Keywords

ASJC Scopus subject areas

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