The reaction of 1-(2,4,6-trimethylphenyl)-1,2-dihydrophosphinine 1-oxides with dimethyl acetylenedicarboxylate; a [4+2] or a [2+2] cycloaddition?

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Abstract

The reaction of dimethyl acetylenedicarboxylate (DMAD) with 3- and 5-methyl-1-aryl-1,2-dihydrophosphinine oxides (6a and 6b, respectively) obtained by the two-step ring enlargement of 2,5-dihydro-1H-phosphole oxide 4 followed different routes. Isomer 6a entered into a [4+2] cycloaddition with DMAD giving, although in low yield, phosphabicyclooctadiene 7, while 6b reacted with the acetylene moiety according to a recently discovered [2+2] protocol to afford spirocyclic oxaphosphete 8. The reaction of isomers 6a and 6b with N-phenylmaleimide under forcing conditions furnished the expected Diels-Alder cycloadducts (10a and 10b, respectively). Hence, depending on the reactant, isomer 6b displayed a dual reactivity.

Original languageEnglish
Pages (from-to)1062-1065
Number of pages4
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number9
Publication statusPublished - 2001

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Cycloaddition
Isomers
Oxides
Acetylene
acetylenedicarboxylic acid dimethyl ester

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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title = "The reaction of 1-(2,4,6-trimethylphenyl)-1,2-dihydrophosphinine 1-oxides with dimethyl acetylenedicarboxylate; a [4+2] or a [2+2] cycloaddition?",
abstract = "The reaction of dimethyl acetylenedicarboxylate (DMAD) with 3- and 5-methyl-1-aryl-1,2-dihydrophosphinine oxides (6a and 6b, respectively) obtained by the two-step ring enlargement of 2,5-dihydro-1H-phosphole oxide 4 followed different routes. Isomer 6a entered into a [4+2] cycloaddition with DMAD giving, although in low yield, phosphabicyclooctadiene 7, while 6b reacted with the acetylene moiety according to a recently discovered [2+2] protocol to afford spirocyclic oxaphosphete 8. The reaction of isomers 6a and 6b with N-phenylmaleimide under forcing conditions furnished the expected Diels-Alder cycloadducts (10a and 10b, respectively). Hence, depending on the reactant, isomer 6b displayed a dual reactivity.",
author = "G. Keglevich and Vask{\'o}, {{\'A} G.} and A. Dob{\'o} and K. Lud{\'a}nyi and L. Tőke",
year = "2001",
language = "English",
pages = "1062--1065",
journal = "Journal of the Chemical Society, Perkin Transactions 1",
issn = "1472-7781",
publisher = "Chemical Society",
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TY - JOUR

T1 - The reaction of 1-(2,4,6-trimethylphenyl)-1,2-dihydrophosphinine 1-oxides with dimethyl acetylenedicarboxylate; a [4+2] or a [2+2] cycloaddition?

AU - Keglevich, G.

AU - Vaskó, Á G.

AU - Dobó, A.

AU - Ludányi, K.

AU - Tőke, L.

PY - 2001

Y1 - 2001

N2 - The reaction of dimethyl acetylenedicarboxylate (DMAD) with 3- and 5-methyl-1-aryl-1,2-dihydrophosphinine oxides (6a and 6b, respectively) obtained by the two-step ring enlargement of 2,5-dihydro-1H-phosphole oxide 4 followed different routes. Isomer 6a entered into a [4+2] cycloaddition with DMAD giving, although in low yield, phosphabicyclooctadiene 7, while 6b reacted with the acetylene moiety according to a recently discovered [2+2] protocol to afford spirocyclic oxaphosphete 8. The reaction of isomers 6a and 6b with N-phenylmaleimide under forcing conditions furnished the expected Diels-Alder cycloadducts (10a and 10b, respectively). Hence, depending on the reactant, isomer 6b displayed a dual reactivity.

AB - The reaction of dimethyl acetylenedicarboxylate (DMAD) with 3- and 5-methyl-1-aryl-1,2-dihydrophosphinine oxides (6a and 6b, respectively) obtained by the two-step ring enlargement of 2,5-dihydro-1H-phosphole oxide 4 followed different routes. Isomer 6a entered into a [4+2] cycloaddition with DMAD giving, although in low yield, phosphabicyclooctadiene 7, while 6b reacted with the acetylene moiety according to a recently discovered [2+2] protocol to afford spirocyclic oxaphosphete 8. The reaction of isomers 6a and 6b with N-phenylmaleimide under forcing conditions furnished the expected Diels-Alder cycloadducts (10a and 10b, respectively). Hence, depending on the reactant, isomer 6b displayed a dual reactivity.

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