Tandem elimination-oxidation of tertiary benzylic alcohols with an oxoammonium salt

Rowan I.L. Meador; Robert E. Anderson; John D. Chisholm

doi:10.1039/d1ob00965f

Tandem elimination-oxidation of tertiary benzylic alcohols with an oxoammonium salt

Rowan I.L. Meador, Robert E. Anderson, John D. Chisholm

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

5 Scopus citations

Abstract

Tertiary benzylic alcohols react with oxoammonium salts, undergoing a tandem elimination/allylic oxidation to provide an allylic ether product in a single step. This mode of reactivity provides a rapid entry into allylic ethers from certain benzylic tertiary alcohols. The allylic ether may be cleaved under reductive conditions to reveal the allylic alcohol.

Original language	English (US)
Pages (from-to)	6233-6236
Number of pages	4
Journal	Organic and Biomolecular Chemistry
Volume	19
Issue number	28
DOIs	https://doi.org/10.1039/d1ob00965f
State	Published - Jul 28 2021

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1039/d1ob00965f

Cite this

@article{c9df6ec328f04102be00717e0bc1a15d,

title = "Tandem elimination-oxidation of tertiary benzylic alcohols with an oxoammonium salt",

abstract = "Tertiary benzylic alcohols react with oxoammonium salts, undergoing a tandem elimination/allylic oxidation to provide an allylic ether product in a single step. This mode of reactivity provides a rapid entry into allylic ethers from certain benzylic tertiary alcohols. The allylic ether may be cleaved under reductive conditions to reveal the allylic alcohol.",

author = "Meador, {Rowan I.L.} and Anderson, {Robert E.} and Chisholm, {John D.}",

note = "Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2021.",

year = "2021",

month = jul,

day = "28",

doi = "10.1039/d1ob00965f",

language = "English (US)",

volume = "19",

pages = "6233--6236",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "28",

}

TY - JOUR

T1 - Tandem elimination-oxidation of tertiary benzylic alcohols with an oxoammonium salt

AU - Meador, Rowan I.L.

AU - Anderson, Robert E.

AU - Chisholm, John D.

N1 - Publisher Copyright: © The Royal Society of Chemistry 2021.

PY - 2021/7/28

Y1 - 2021/7/28

N2 - Tertiary benzylic alcohols react with oxoammonium salts, undergoing a tandem elimination/allylic oxidation to provide an allylic ether product in a single step. This mode of reactivity provides a rapid entry into allylic ethers from certain benzylic tertiary alcohols. The allylic ether may be cleaved under reductive conditions to reveal the allylic alcohol.

AB - Tertiary benzylic alcohols react with oxoammonium salts, undergoing a tandem elimination/allylic oxidation to provide an allylic ether product in a single step. This mode of reactivity provides a rapid entry into allylic ethers from certain benzylic tertiary alcohols. The allylic ether may be cleaved under reductive conditions to reveal the allylic alcohol.

UR - http://www.scopus.com/inward/record.url?scp=85111137956&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85111137956&partnerID=8YFLogxK

U2 - 10.1039/d1ob00965f

DO - 10.1039/d1ob00965f

M3 - Article

C2 - 34231623

AN - SCOPUS:85111137956

SN - 1477-0520

VL - 19

SP - 6233

EP - 6236

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 28

ER -

Tandem elimination-oxidation of tertiary benzylic alcohols with an oxoammonium salt

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this