Perfect switching of photoreactivity by acid: Photochemical decarboxylation versus transesterification of mesityl cyclohexanecarboxylate

Tadashi Mori; Takehiko Wada; Yoshihisa Inoue

doi:10.1021/ol0065266

Perfect switching of photoreactivity by acid: Photochemical decarboxylation versus transesterification of mesityl cyclohexanecarboxylate

Tadashi Mori, Takehiko Wada, Yoshihisa Inoue

IMRAM - Division of Organic- and Biomaterials Research

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

30 Citations (Scopus)

Abstract

(matrix presented) Mesityl cyclohexanecarboxylate has been photodecarboxylated upon excitation at 254 nm to form cyclohexylmesitylene in good yield in neutral acetonitrile solutions. In the presence of a catalytic amount of the acid and ethanol as a nucleophile, however, the same compound undergoes facile transesterification upon irradiation, affording its ethyl ester in almost quantitative yield.

Original language	English
Pages (from-to)	3401-3404
Number of pages	4
Journal	Organic Letters
Volume	2
Issue number	21
DOIs	https://doi.org/10.1021/ol0065266
Publication status	Published - 2000 Oct 19

Access to Document

10.1021/ol0065266

Cite this

@article{397cd487ce344cd8beec49a1a23e7e58,

title = "Perfect switching of photoreactivity by acid: Photochemical decarboxylation versus transesterification of mesityl cyclohexanecarboxylate",

abstract = "(matrix presented) Mesityl cyclohexanecarboxylate has been photodecarboxylated upon excitation at 254 nm to form cyclohexylmesitylene in good yield in neutral acetonitrile solutions. In the presence of a catalytic amount of the acid and ethanol as a nucleophile, however, the same compound undergoes facile transesterification upon irradiation, affording its ethyl ester in almost quantitative yield.",

author = "Tadashi Mori and Takehiko Wada and Yoshihisa Inoue",

year = "2000",

month = oct,

day = "19",

doi = "10.1021/ol0065266",

language = "English",

volume = "2",

pages = "3401--3404",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "21",

}

TY - JOUR

T1 - Perfect switching of photoreactivity by acid

T2 - Photochemical decarboxylation versus transesterification of mesityl cyclohexanecarboxylate

AU - Mori, Tadashi

AU - Wada, Takehiko

AU - Inoue, Yoshihisa

PY - 2000/10/19

Y1 - 2000/10/19

N2 - (matrix presented) Mesityl cyclohexanecarboxylate has been photodecarboxylated upon excitation at 254 nm to form cyclohexylmesitylene in good yield in neutral acetonitrile solutions. In the presence of a catalytic amount of the acid and ethanol as a nucleophile, however, the same compound undergoes facile transesterification upon irradiation, affording its ethyl ester in almost quantitative yield.

AB - (matrix presented) Mesityl cyclohexanecarboxylate has been photodecarboxylated upon excitation at 254 nm to form cyclohexylmesitylene in good yield in neutral acetonitrile solutions. In the presence of a catalytic amount of the acid and ethanol as a nucleophile, however, the same compound undergoes facile transesterification upon irradiation, affording its ethyl ester in almost quantitative yield.

UR - http://www.scopus.com/inward/record.url?scp=0001323365&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0001323365&partnerID=8YFLogxK

U2 - 10.1021/ol0065266

DO - 10.1021/ol0065266

M3 - Article

AN - SCOPUS:0001323365

SN - 1523-7060

VL - 2

SP - 3401

EP - 3404

JO - Organic Letters

JF - Organic Letters

IS - 21

ER -

Perfect switching of photoreactivity by acid: Photochemical decarboxylation versus transesterification of mesityl cyclohexanecarboxylate

Abstract

Access to Document

Other files and links

Fingerprint

Cite this