Intramolecular interception of the Newman-Kwart rearrangement by carboxylic acids

Timothy A. Ablott; Mitchell G. Fishburn; David R. Turner; Christopher Richardson

doi:10.1016/j.tetlet.2020.152153

Intramolecular interception of the Newman-Kwart rearrangement by carboxylic acids

Timothy A. Ablott, Mitchell G. Fishburn, David R. Turner, Christopher Richardson

School of Chemistry

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

1 Citation (Scopus)

Abstract

Instead of undergoing the Newman-Kwart rearrangement, thermally-promoted reactions of O-aryl dimethylthiocarbamates featuring ortho-carboxylic acid substituents result in the loss of carbonylsulfide and formation of N,N-dimethylsalicylamides in high yields.

Original language	English
Article number	152153
Number of pages	4
Journal	Tetrahedron Letters
Volume	61
Issue number	30
DOIs	https://doi.org/10.1016/j.tetlet.2020.152153
Publication status	Published - 23 Jul 2020

Keywords

Metal-organic framework
Microwave-assisted synthesis
Newman-Kwart rearrangement
Thermal reaction

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10.1016/j.tetlet.2020.152153

Cite this

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title = "Intramolecular interception of the Newman-Kwart rearrangement by carboxylic acids",

abstract = "Instead of undergoing the Newman-Kwart rearrangement, thermally-promoted reactions of O-aryl dimethylthiocarbamates featuring ortho-carboxylic acid substituents result in the loss of carbonylsulfide and formation of N,N-dimethylsalicylamides in high yields.",

keywords = "Metal-organic framework, Microwave-assisted synthesis, Newman-Kwart rearrangement, Thermal reaction",

author = "Ablott, {Timothy A.} and Fishburn, {Mitchell G.} and Turner, {David R.} and Christopher Richardson",

year = "2020",

month = jul,

day = "23",

doi = "10.1016/j.tetlet.2020.152153",

language = "English",

volume = "61",

journal = "Tetrahedron Letters",

issn = "0040-4039",

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T1 - Intramolecular interception of the Newman-Kwart rearrangement by carboxylic acids

AU - Ablott, Timothy A.

AU - Fishburn, Mitchell G.

AU - Turner, David R.

AU - Richardson, Christopher

PY - 2020/7/23

Y1 - 2020/7/23

N2 - Instead of undergoing the Newman-Kwart rearrangement, thermally-promoted reactions of O-aryl dimethylthiocarbamates featuring ortho-carboxylic acid substituents result in the loss of carbonylsulfide and formation of N,N-dimethylsalicylamides in high yields.

AB - Instead of undergoing the Newman-Kwart rearrangement, thermally-promoted reactions of O-aryl dimethylthiocarbamates featuring ortho-carboxylic acid substituents result in the loss of carbonylsulfide and formation of N,N-dimethylsalicylamides in high yields.

KW - Metal-organic framework

KW - Microwave-assisted synthesis

KW - Newman-Kwart rearrangement

KW - Thermal reaction

UR - http://www.scopus.com/inward/record.url?scp=85086935533&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2020.152153

DO - 10.1016/j.tetlet.2020.152153

M3 - Article

AN - SCOPUS:85086935533

VL - 61

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 30

M1 - 152153

ER -

Intramolecular interception of the Newman-Kwart rearrangement by carboxylic acids

Abstract

Keywords

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Australian Synchrotron

Cite this

Intramolecular interception of the Newman-Kwart rearrangement by carboxylic acids

Abstract

Keywords

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Equipment

Australian Synchrotron

Cite this