Synthesis of 4,6-dimethyldibenzothiophene and 1,2,3,4-tetrahydro-4,6- dimethyldibenzothiophene via Tilak annulation

Xiaoying Xu; Xiang Li; Anjie Wang; Yinyong Sun; W. Bernd Schweizer; Roel Prins

doi:10.1002/hlca.201100191

Synthesis of 4,6-dimethyldibenzothiophene and 1,2,3,4-tetrahydro-4,6- dimethyldibenzothiophene via Tilak annulation

Xiaoying Xu
, Xiang Li
, Anjie Wang
, Yinyong Sun
, W. Bernd Schweizer
, Roel Prins^*

^*Corresponding author for this work

Dalian University of Technology
Liaoning Key Laboratory of Petrochemical Technology and Equipments
School of Chemistry and Chemical Engineering, Harbin Institute of Technology
ETH Zurich

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

8 Scopus citations

Abstract

1,2,3,4-Tetrahydro-4,6-dimethyldibenzothiophene was prepared by coupling 2-bromo-3-methylcyclohexanone with 2-methylbenzenethiol and annulating the product with the aid of polyphosphoric acid. A mixture of 1,2,3,4-tetrahydro-4, 6-dimethyldibenzothiophene and 4,6-dimethyldibenzothiophene was prepared by coupling 2-bromo-3-methylcyclohex-2-en-1-one with 2-methylbenzenethiol and annulating the product with the aid of polyphosphoric acid. 2-Bromo-3- methylcyclohexanone was synthesized by conjugate addition of Me₃Al to 2-bromocyclohex-2-en-1-one with CuBr as catalyst and 2-bromo-3-methylcyclohex- 2-en-1-one by bromination-elimination of 3-methylcyclohex-2-en-1-one. 1,2,3,4,4a,9b-Hexahydro-4,6-dimethyldibenzothiophene was prepared by reduction of 1,2,3,4-tetrahydro-4,6-dimethyldibenzothiophene with Zn and CF ₃COOH.

Original language	English
Pages (from-to)	1754-1763
Number of pages	10
Journal	Helvetica Chimica Acta
Volume	94
Issue number	10
DOIs	https://doi.org/10.1002/hlca.201100191
State	Published - Oct 2011
Externally published	Yes

Keywords

Cyclohex-2-en-1-one, 2-bromo-3-methyl-
Cyclohexanone, 2-bromo-3-methyl-
Dibenzothiophene, 1,2,3,4-tetrahydro-4,6-dimethyl-
Dibenzothiophene, 4,6-dimethyl-
Tilak annulation
X-Ray crystallography

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10.1002/hlca.201100191

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@article{d52f1089077a438999b75bb196aa9004,

title = "Synthesis of 4,6-dimethyldibenzothiophene and 1,2,3,4-tetrahydro-4,6- dimethyldibenzothiophene via Tilak annulation",

abstract = "1,2,3,4-Tetrahydro-4,6-dimethyldibenzothiophene was prepared by coupling 2-bromo-3-methylcyclohexanone with 2-methylbenzenethiol and annulating the product with the aid of polyphosphoric acid. A mixture of 1,2,3,4-tetrahydro-4, 6-dimethyldibenzothiophene and 4,6-dimethyldibenzothiophene was prepared by coupling 2-bromo-3-methylcyclohex-2-en-1-one with 2-methylbenzenethiol and annulating the product with the aid of polyphosphoric acid. 2-Bromo-3- methylcyclohexanone was synthesized by conjugate addition of Me3Al to 2-bromocyclohex-2-en-1-one with CuBr as catalyst and 2-bromo-3-methylcyclohex- 2-en-1-one by bromination-elimination of 3-methylcyclohex-2-en-1-one. 1,2,3,4,4a,9b-Hexahydro-4,6-dimethyldibenzothiophene was prepared by reduction of 1,2,3,4-tetrahydro-4,6-dimethyldibenzothiophene with Zn and CF 3COOH.",

keywords = "Cyclohex-2-en-1-one, 2-bromo-3-methyl-, Cyclohexanone, 2-bromo-3-methyl-, Dibenzothiophene, 1,2,3,4-tetrahydro-4,6-dimethyl-, Dibenzothiophene, 4,6-dimethyl-, Tilak annulation, X-Ray crystallography",

author = "Xiaoying Xu and Xiang Li and Anjie Wang and Yinyong Sun and Schweizer, \{W. Bernd\} and Roel Prins",

year = "2011",

month = oct,

doi = "10.1002/hlca.201100191",

language = "英语",

volume = "94",

pages = "1754--1763",

journal = "Helvetica Chimica Acta",

issn = "0018-019X",

publisher = "Wiley-Blackwell",

number = "10",

}

TY - JOUR

T1 - Synthesis of 4,6-dimethyldibenzothiophene and 1,2,3,4-tetrahydro-4,6- dimethyldibenzothiophene via Tilak annulation

AU - Xu, Xiaoying

AU - Li, Xiang

AU - Wang, Anjie

AU - Sun, Yinyong

AU - Schweizer, W. Bernd

AU - Prins, Roel

PY - 2011/10

Y1 - 2011/10

N2 - 1,2,3,4-Tetrahydro-4,6-dimethyldibenzothiophene was prepared by coupling 2-bromo-3-methylcyclohexanone with 2-methylbenzenethiol and annulating the product with the aid of polyphosphoric acid. A mixture of 1,2,3,4-tetrahydro-4, 6-dimethyldibenzothiophene and 4,6-dimethyldibenzothiophene was prepared by coupling 2-bromo-3-methylcyclohex-2-en-1-one with 2-methylbenzenethiol and annulating the product with the aid of polyphosphoric acid. 2-Bromo-3- methylcyclohexanone was synthesized by conjugate addition of Me3Al to 2-bromocyclohex-2-en-1-one with CuBr as catalyst and 2-bromo-3-methylcyclohex- 2-en-1-one by bromination-elimination of 3-methylcyclohex-2-en-1-one. 1,2,3,4,4a,9b-Hexahydro-4,6-dimethyldibenzothiophene was prepared by reduction of 1,2,3,4-tetrahydro-4,6-dimethyldibenzothiophene with Zn and CF 3COOH.

AB - 1,2,3,4-Tetrahydro-4,6-dimethyldibenzothiophene was prepared by coupling 2-bromo-3-methylcyclohexanone with 2-methylbenzenethiol and annulating the product with the aid of polyphosphoric acid. A mixture of 1,2,3,4-tetrahydro-4, 6-dimethyldibenzothiophene and 4,6-dimethyldibenzothiophene was prepared by coupling 2-bromo-3-methylcyclohex-2-en-1-one with 2-methylbenzenethiol and annulating the product with the aid of polyphosphoric acid. 2-Bromo-3- methylcyclohexanone was synthesized by conjugate addition of Me3Al to 2-bromocyclohex-2-en-1-one with CuBr as catalyst and 2-bromo-3-methylcyclohex- 2-en-1-one by bromination-elimination of 3-methylcyclohex-2-en-1-one. 1,2,3,4,4a,9b-Hexahydro-4,6-dimethyldibenzothiophene was prepared by reduction of 1,2,3,4-tetrahydro-4,6-dimethyldibenzothiophene with Zn and CF 3COOH.

KW - Cyclohex-2-en-1-one, 2-bromo-3-methyl-

KW - Cyclohexanone, 2-bromo-3-methyl-

KW - Dibenzothiophene, 1,2,3,4-tetrahydro-4,6-dimethyl-

KW - Dibenzothiophene, 4,6-dimethyl-

KW - Tilak annulation

KW - X-Ray crystallography

UR - https://www.scopus.com/pages/publications/80054970532

U2 - 10.1002/hlca.201100191

DO - 10.1002/hlca.201100191

M3 - 文章

AN - SCOPUS:80054970532

SN - 0018-019X

VL - 94

SP - 1754

EP - 1763

JO - Helvetica Chimica Acta

JF - Helvetica Chimica Acta

IS - 10

ER -

Synthesis of 4,6-dimethyldibenzothiophene and 1,2,3,4-tetrahydro-4,6- dimethyldibenzothiophene via Tilak annulation

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Keywords

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