Formation of hydrindans and tricyclo[4.3.0.03,8]nonanes via 6-endo trapping of the Nazarov oxyallyl intermediate

C. C. Browder; F. G. West

doi:10.1055/s-1999-32132

Formation of hydrindans and tricyclo[4.3.0.0^3,8]nonanes via 6-endo trapping of the Nazarov oxyallyl intermediate

C. C. Browder, F. G. West

Chemistry and Biochemistry

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

28 Scopus citations

Abstract

Treatment of trienones 1a-g with BF₃·OEt₂ at -78°C followed by warming effected Nazarov electrocyclization followed by 6-endo cation-olefin cyclization. The resulting tertiary carbocations underwent elimination to give olefinic products 2, intramolecular hydride transfer to furnish enones 3 and/or 3+2 ring-closure providing tricyclic products 4. Use of TiCl₄ in place of BF₃·OEt₂ led in most cases to a mixture of enones 3 and chloride- trapping products 7.

Original language	English (US)
Pages (from-to)	1363-1366
Number of pages	4
Journal	Synlett
Issue number	9
DOIs	https://doi.org/10.1055/s-1999-32132
State	Published - 1999

Keywords

Cyclizations
Domino reactions
Polycycles
Ring closure
Tandem reactions

ASJC Scopus subject areas

Organic Chemistry

Access to Document

10.1055/s-1999-32132

Cite this

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title = "Formation of hydrindans and tricyclo[4.3.0.03,8]nonanes via 6-endo trapping of the Nazarov oxyallyl intermediate",

abstract = "Treatment of trienones 1a-g with BF3·OEt2 at -78°C followed by warming effected Nazarov electrocyclization followed by 6-endo cation-olefin cyclization. The resulting tertiary carbocations underwent elimination to give olefinic products 2, intramolecular hydride transfer to furnish enones 3 and/or 3+2 ring-closure providing tricyclic products 4. Use of TiCl4 in place of BF3·OEt2 led in most cases to a mixture of enones 3 and chloride- trapping products 7.",

keywords = "Cyclizations, Domino reactions, Polycycles, Ring closure, Tandem reactions",

author = "Browder, {C. C.} and West, {F. G.}",

year = "1999",

doi = "10.1055/s-1999-32132",

language = "English (US)",

pages = "1363--1366",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "9",

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T1 - Formation of hydrindans and tricyclo[4.3.0.03,8]nonanes via 6-endo trapping of the Nazarov oxyallyl intermediate

AU - Browder, C. C.

AU - West, F. G.

PY - 1999

Y1 - 1999

N2 - Treatment of trienones 1a-g with BF3·OEt2 at -78°C followed by warming effected Nazarov electrocyclization followed by 6-endo cation-olefin cyclization. The resulting tertiary carbocations underwent elimination to give olefinic products 2, intramolecular hydride transfer to furnish enones 3 and/or 3+2 ring-closure providing tricyclic products 4. Use of TiCl4 in place of BF3·OEt2 led in most cases to a mixture of enones 3 and chloride- trapping products 7.

AB - Treatment of trienones 1a-g with BF3·OEt2 at -78°C followed by warming effected Nazarov electrocyclization followed by 6-endo cation-olefin cyclization. The resulting tertiary carbocations underwent elimination to give olefinic products 2, intramolecular hydride transfer to furnish enones 3 and/or 3+2 ring-closure providing tricyclic products 4. Use of TiCl4 in place of BF3·OEt2 led in most cases to a mixture of enones 3 and chloride- trapping products 7.

KW - Cyclizations

KW - Domino reactions

KW - Polycycles

KW - Ring closure

KW - Tandem reactions

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DO - 10.1055/s-1999-32132

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JF - Synlett

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