Diene-yne cyclisation reactions of 1-ethynyl-2-vinyl-3,4- dihydronaphthalenes and 1-ethynyl-2-vinylnaphthalenes

Masataka Watanabe; Kodai Shiine; Keiko Ldeta; Taisuke Matsumoto; Thies Thiemann

doi:10.3184/030823408X375214

Diene-yne cyclisation reactions of 1-ethynyl-2-vinyl-3,4- dihydronaphthalenes and 1-ethynyl-2-vinylnaphthalenes

Masataka Watanabe, Kodai Shiine, Keiko Ldeta, Taisuke Matsumoto, Thies Thiemann

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

9 Citations (Scopus)

Abstract

The reaction of 1-ethynyl-2-vinyl-3,4-dihydronaphthalenes and 1-ethynyl-2-vinylnaphthalenes over RuCI₂(p-cymene) PPh₃ leads to 9,10-dihydrophenanthrenes and phenanthrenes in those cases where the ethynyl group in the substrates carries a terminal proton. When 1-phenylethynyl-2-vinyl-3,4-dihydronaphthalenes or 1-phenylethynyl-2- vinylnaphthalenes are reacted over Pt(PPh₃)₄, 1-methylene-1H-benz[e]-4,5-dihydroindenes and 1-methylene-1H-benz[e]indenes are formed.

Original language	English
Pages (from-to)	669-678
Number of pages	10
Journal	Journal of Chemical Research
Issue number	12
DOIs	https://doi.org/10.3184/030823408X375214
Publication status	Published - Dec 2008
Externally published	Yes

Keywords

Catalysis
Cyclisation
Diene-ynes
Fulvenes
Platinum
Ruthenium

ASJC Scopus subject areas

Chemistry(all)

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10.3184/030823408X375214

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title = "Diene-yne cyclisation reactions of 1-ethynyl-2-vinyl-3,4- dihydronaphthalenes and 1-ethynyl-2-vinylnaphthalenes",

abstract = "The reaction of 1-ethynyl-2-vinyl-3,4-dihydronaphthalenes and 1-ethynyl-2-vinylnaphthalenes over RuCI2(p-cymene) PPh3 leads to 9,10-dihydrophenanthrenes and phenanthrenes in those cases where the ethynyl group in the substrates carries a terminal proton. When 1-phenylethynyl-2-vinyl-3,4-dihydronaphthalenes or 1-phenylethynyl-2- vinylnaphthalenes are reacted over Pt(PPh3)4, 1-methylene-1H-benz[e]-4,5-dihydroindenes and 1-methylene-1H-benz[e]indenes are formed.",

keywords = "Catalysis, Cyclisation, Diene-ynes, Fulvenes, Platinum, Ruthenium",

author = "Masataka Watanabe and Kodai Shiine and Keiko Ldeta and Taisuke Matsumoto and Thies Thiemann",

year = "2008",

month = dec,

doi = "10.3184/030823408X375214",

language = "English",

pages = "669--678",

journal = "Journal of Chemical Research",

issn = "0308-2342",

publisher = "Science Reviews Ltd",

number = "12",

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TY - JOUR

T1 - Diene-yne cyclisation reactions of 1-ethynyl-2-vinyl-3,4- dihydronaphthalenes and 1-ethynyl-2-vinylnaphthalenes

AU - Watanabe, Masataka

AU - Shiine, Kodai

AU - Ldeta, Keiko

AU - Matsumoto, Taisuke

AU - Thiemann, Thies

PY - 2008/12

Y1 - 2008/12

N2 - The reaction of 1-ethynyl-2-vinyl-3,4-dihydronaphthalenes and 1-ethynyl-2-vinylnaphthalenes over RuCI2(p-cymene) PPh3 leads to 9,10-dihydrophenanthrenes and phenanthrenes in those cases where the ethynyl group in the substrates carries a terminal proton. When 1-phenylethynyl-2-vinyl-3,4-dihydronaphthalenes or 1-phenylethynyl-2- vinylnaphthalenes are reacted over Pt(PPh3)4, 1-methylene-1H-benz[e]-4,5-dihydroindenes and 1-methylene-1H-benz[e]indenes are formed.

AB - The reaction of 1-ethynyl-2-vinyl-3,4-dihydronaphthalenes and 1-ethynyl-2-vinylnaphthalenes over RuCI2(p-cymene) PPh3 leads to 9,10-dihydrophenanthrenes and phenanthrenes in those cases where the ethynyl group in the substrates carries a terminal proton. When 1-phenylethynyl-2-vinyl-3,4-dihydronaphthalenes or 1-phenylethynyl-2- vinylnaphthalenes are reacted over Pt(PPh3)4, 1-methylene-1H-benz[e]-4,5-dihydroindenes and 1-methylene-1H-benz[e]indenes are formed.

KW - Catalysis

KW - Cyclisation

KW - Diene-ynes

KW - Fulvenes

KW - Platinum

KW - Ruthenium

UR - http://www.scopus.com/inward/record.url?scp=58249098894&partnerID=8YFLogxK

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M3 - Article

AN - SCOPUS:58249098894

SN - 0308-2342

SP - 669

EP - 678

JO - Journal of Chemical Research

JF - Journal of Chemical Research

IS - 12

ER -

Diene-yne cyclisation reactions of 1-ethynyl-2-vinyl-3,4- dihydronaphthalenes and 1-ethynyl-2-vinylnaphthalenes

Abstract

Keywords

ASJC Scopus subject areas

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