Oxone-acetone mediated Wacker-type oxidation of benzo-fused olefins

Ravindra S. Phatake; Chepuri V. Ramana

doi:10.1016/j.tetlet.2015.04.102

Oxone-acetone mediated Wacker-type oxidation of benzo-fused olefins

Ravindra S. Phatake, Chepuri V. Ramana

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

13 Scopus citations

Abstract

Herein we disclose a novel application of the oxone-acetone combination for the Wacker-type oxidation of indenes and dihydronaphthalenes leading, respectively, to indan-2-ones and 2-tetralones. The amount of the base employed in the reaction seems to switch the reaction path from dioxygenation to Wacker-type oxidation. Control experiments suggest that the reaction is not proceeding via the epoxide route and also that there is no role of trace amounts of metals present in the reagents on the current oxidation.

Original language	English
Pages (from-to)	3868-3871
Number of pages	4
Journal	Tetrahedron Letters
Volume	56
Issue number	25
DOIs	https://doi.org/10.1016/j.tetlet.2015.04.102
State	Published - 30 May 2015
Externally published	Yes

Keywords

Dihydronaphthalene
Indene
Oxone
Wacker oxidation

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2015.04.102

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title = "Oxone-acetone mediated Wacker-type oxidation of benzo-fused olefins",

abstract = "Herein we disclose a novel application of the oxone-acetone combination for the Wacker-type oxidation of indenes and dihydronaphthalenes leading, respectively, to indan-2-ones and 2-tetralones. The amount of the base employed in the reaction seems to switch the reaction path from dioxygenation to Wacker-type oxidation. Control experiments suggest that the reaction is not proceeding via the epoxide route and also that there is no role of trace amounts of metals present in the reagents on the current oxidation.",

keywords = "Dihydronaphthalene, Indene, Oxone, Wacker oxidation",

author = "Phatake, \{Ravindra S.\} and Ramana, \{Chepuri V.\}",

year = "2015",

month = may,

day = "30",

doi = "10.1016/j.tetlet.2015.04.102",

language = "English",

volume = "56",

pages = "3868--3871",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd.",

number = "25",

}

TY - JOUR

T1 - Oxone-acetone mediated Wacker-type oxidation of benzo-fused olefins

AU - Phatake, Ravindra S.

AU - Ramana, Chepuri V.

PY - 2015/5/30

Y1 - 2015/5/30

N2 - Herein we disclose a novel application of the oxone-acetone combination for the Wacker-type oxidation of indenes and dihydronaphthalenes leading, respectively, to indan-2-ones and 2-tetralones. The amount of the base employed in the reaction seems to switch the reaction path from dioxygenation to Wacker-type oxidation. Control experiments suggest that the reaction is not proceeding via the epoxide route and also that there is no role of trace amounts of metals present in the reagents on the current oxidation.

AB - Herein we disclose a novel application of the oxone-acetone combination for the Wacker-type oxidation of indenes and dihydronaphthalenes leading, respectively, to indan-2-ones and 2-tetralones. The amount of the base employed in the reaction seems to switch the reaction path from dioxygenation to Wacker-type oxidation. Control experiments suggest that the reaction is not proceeding via the epoxide route and also that there is no role of trace amounts of metals present in the reagents on the current oxidation.

KW - Dihydronaphthalene

KW - Indene

KW - Oxone

KW - Wacker oxidation

UR - https://www.scopus.com/pages/publications/84930178970

U2 - 10.1016/j.tetlet.2015.04.102

DO - 10.1016/j.tetlet.2015.04.102

M3 - Article

AN - SCOPUS:84930178970

SN - 0040-4039

VL - 56

SP - 3868

EP - 3871

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 25

ER -

Oxone-acetone mediated Wacker-type oxidation of benzo-fused olefins

Abstract

Keywords

ASJC Scopus subject areas

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