A novel approach to 5,5'-diisopropyl-3,3'-BI-2H-cyclohepta[b]furan-2-one

Noboru Morita; Junya Higashi; Kazuyuki Okada; Taku Shoji; Kozo Toyota; Masataka Watanabe; Masafumi Yasunami; Shigeru Kikuchi; Shunji Ito

doi:10.3987/COM-07-S(U)43

A novel approach to 5,5'-diisopropyl-3,3'-BI-2H-cyclohepta[b]furan-2-one

Noboru Morita, Junya Higashi, Kazuyuki Okada, Taku Shoji, Kozo Toyota, Masataka Watanabe, Masafumi Yasunami, Shigeru Kikuchi, Shunji Ito

SCI - Chemistry

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

4 Citations (Scopus)

Abstract

5-Isopropyl-2H-cyclohepta[b]furan-2-one (1) reacted with DMSD to give dimethyl(5-isopropyl-2-oxo-2H-cyclohepta[b] furan-3-yl)sulfonium trifluoromethane-sulfonate(2), which was treated with Et₃N to give 5-isopropyl-3-methylthio-2H-cyclohepta[b]furan-2-one (3). Sulfide 3 was oxidized with mCPBA to give sulfoxide 4 and sulfone 5. The salt 6 which comes from the treatment of 4 with Tf₂O converted to an unexpected product, 5,5'-diisopropyl-3,3'-bi-2H-cyclohepta[b]furan-2-one(7), thermally.

Original language	English
Pages (from-to)	237-240
Number of pages	4
Journal	Heterocycles
Volume	73
Issue number	C
DOIs	https://doi.org/10.3987/COM-07-S(U)43
Publication status	Published - 2007

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

Access to Document

10.3987/COM-07-S(U)43

Cite this

@article{b2969d52369c435c873753cdcfceb9b5,

title = "A novel approach to 5,5'-diisopropyl-3,3'-BI-2H-cyclohepta[b]furan-2-one",

abstract = "5-Isopropyl-2H-cyclohepta[b]furan-2-one (1) reacted with DMSD to give dimethyl(5-isopropyl-2-oxo-2H-cyclohepta[b] furan-3-yl)sulfonium trifluoromethane-sulfonate(2), which was treated with Et3N to give 5-isopropyl-3-methylthio-2H-cyclohepta[b]furan-2-one (3). Sulfide 3 was oxidized with mCPBA to give sulfoxide 4 and sulfone 5. The salt 6 which comes from the treatment of 4 with Tf2O converted to an unexpected product, 5,5'-diisopropyl-3,3'-bi-2H-cyclohepta[b]furan-2-one(7), thermally.",

author = "Noboru Morita and Junya Higashi and Kazuyuki Okada and Taku Shoji and Kozo Toyota and Masataka Watanabe and Masafumi Yasunami and Shigeru Kikuchi and Shunji Ito",

year = "2007",

doi = "10.3987/COM-07-S(U)43",

language = "English",

volume = "73",

pages = "237--240",

journal = "Heterocycles",

issn = "0385-5414",

publisher = "Japan Institute of Heterocyclic Chemistry",

number = "C",

}

TY - JOUR

T1 - A novel approach to 5,5'-diisopropyl-3,3'-BI-2H-cyclohepta[b]furan-2-one

AU - Morita, Noboru

AU - Higashi, Junya

AU - Okada, Kazuyuki

AU - Shoji, Taku

AU - Toyota, Kozo

AU - Watanabe, Masataka

AU - Yasunami, Masafumi

AU - Kikuchi, Shigeru

AU - Ito, Shunji

PY - 2007

Y1 - 2007

N2 - 5-Isopropyl-2H-cyclohepta[b]furan-2-one (1) reacted with DMSD to give dimethyl(5-isopropyl-2-oxo-2H-cyclohepta[b] furan-3-yl)sulfonium trifluoromethane-sulfonate(2), which was treated with Et3N to give 5-isopropyl-3-methylthio-2H-cyclohepta[b]furan-2-one (3). Sulfide 3 was oxidized with mCPBA to give sulfoxide 4 and sulfone 5. The salt 6 which comes from the treatment of 4 with Tf2O converted to an unexpected product, 5,5'-diisopropyl-3,3'-bi-2H-cyclohepta[b]furan-2-one(7), thermally.

AB - 5-Isopropyl-2H-cyclohepta[b]furan-2-one (1) reacted with DMSD to give dimethyl(5-isopropyl-2-oxo-2H-cyclohepta[b] furan-3-yl)sulfonium trifluoromethane-sulfonate(2), which was treated with Et3N to give 5-isopropyl-3-methylthio-2H-cyclohepta[b]furan-2-one (3). Sulfide 3 was oxidized with mCPBA to give sulfoxide 4 and sulfone 5. The salt 6 which comes from the treatment of 4 with Tf2O converted to an unexpected product, 5,5'-diisopropyl-3,3'-bi-2H-cyclohepta[b]furan-2-one(7), thermally.

UR - http://www.scopus.com/inward/record.url?scp=45149110487&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=45149110487&partnerID=8YFLogxK

U2 - 10.3987/COM-07-S(U)43

DO - 10.3987/COM-07-S(U)43

M3 - Article

AN - SCOPUS:45149110487

SN - 0385-5414

VL - 73

SP - 237

EP - 240

JO - Heterocycles

JF - Heterocycles

IS - C

ER -

A novel approach to 5,5'-diisopropyl-3,3'-BI-2H-cyclohepta[b]furan-2-one

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this