Some Cycloaddition Reactions of 5,8-Dimethoxynaphtho[2,3-c]furan-4,9-dione

Matthew Piggott; Dieter Wege

doi:10.1071/C98031

Some Cycloaddition Reactions of 5,8-Dimethoxynaphtho[2,3-c]furan-4,9-dione

Matthew Piggott, Dieter Wege

Research output: Contribution to journal › Article

5 Citations (Scopus)

Abstract

Methylation of 5,8-dihydroxynaphtho[2,3-c]furan-4,9-dione (5) gave, in addition to the title ether (7), the fragmentation products 4-hydroxy-1,5,8-trimethoxy-3-methylnaphthalene-2-carbaldehyde (8) and its methyl ether (9). Addition of benzyne to (7) afforded mainly the expected [4+2] cycloadduct (15) and minor amounts of adduct (16), derived by addition of (7) to (15), and adduct (19), derived by a homo- or 1,3-addition of benzyne to (15), followed by decarbonylation. Adducts of (7) with 1,4-dihydro-1,4-epoxynaphthalene and dimethyl acetylenedicarboxylate also were prepared.

Original language	English
Pages (from-to)	819-824
Journal	Australian Journal of Chemistry: an international journal for chemical science
Volume	51
Issue number	N/A
DOIs	https://doi.org/10.1071/C98031
Publication status	Published - 1998

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@article{086a0bf2926041a9b231f0d455c72de1,

title = "Some Cycloaddition Reactions of 5,8-Dimethoxynaphtho[2,3-c]furan-4,9-dione",

abstract = "Methylation of 5,8-dihydroxynaphtho[2,3-c]furan-4,9-dione (5) gave, in addition to the title ether (7), the fragmentation products 4-hydroxy-1,5,8-trimethoxy-3-methylnaphthalene-2-carbaldehyde (8) and its methyl ether (9). Addition of benzyne to (7) afforded mainly the expected [4+2] cycloadduct (15) and minor amounts of adduct (16), derived by addition of (7) to (15), and adduct (19), derived by a homo- or 1,3-addition of benzyne to (15), followed by decarbonylation. Adducts of (7) with 1,4-dihydro-1,4-epoxynaphthalene and dimethyl acetylenedicarboxylate also were prepared.",

author = "Matthew Piggott and Dieter Wege",

year = "1998",

doi = "10.1071/C98031",

language = "English",

volume = "51",

pages = "819--824",

journal = "Australian Journal of Chemistry:an international journal for chemical science",

issn = "0004-9425",

publisher = "CSIRO Publishing",

number = "N/A",

}

TY - JOUR

T1 - Some Cycloaddition Reactions of 5,8-Dimethoxynaphtho[2,3-c]furan-4,9-dione

AU - Piggott, Matthew

AU - Wege, Dieter

PY - 1998

Y1 - 1998

N2 - Methylation of 5,8-dihydroxynaphtho[2,3-c]furan-4,9-dione (5) gave, in addition to the title ether (7), the fragmentation products 4-hydroxy-1,5,8-trimethoxy-3-methylnaphthalene-2-carbaldehyde (8) and its methyl ether (9). Addition of benzyne to (7) afforded mainly the expected [4+2] cycloadduct (15) and minor amounts of adduct (16), derived by addition of (7) to (15), and adduct (19), derived by a homo- or 1,3-addition of benzyne to (15), followed by decarbonylation. Adducts of (7) with 1,4-dihydro-1,4-epoxynaphthalene and dimethyl acetylenedicarboxylate also were prepared.

AB - Methylation of 5,8-dihydroxynaphtho[2,3-c]furan-4,9-dione (5) gave, in addition to the title ether (7), the fragmentation products 4-hydroxy-1,5,8-trimethoxy-3-methylnaphthalene-2-carbaldehyde (8) and its methyl ether (9). Addition of benzyne to (7) afforded mainly the expected [4+2] cycloadduct (15) and minor amounts of adduct (16), derived by addition of (7) to (15), and adduct (19), derived by a homo- or 1,3-addition of benzyne to (15), followed by decarbonylation. Adducts of (7) with 1,4-dihydro-1,4-epoxynaphthalene and dimethyl acetylenedicarboxylate also were prepared.

U2 - 10.1071/C98031

DO - 10.1071/C98031

M3 - Article

VL - 51

SP - 819

EP - 824

JO - Australian Journal of Chemistry:an international journal for chemical science

JF - Australian Journal of Chemistry:an international journal for chemical science

SN - 0004-9425

IS - N/A

ER -