Synthesis of phosphine-borane complexes of P-heterocycles

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Abstract

Dihydro-1H-phosphole-boranes 5 and 10 were prepared from phosphine oxides 1 and 9 respectively. Reaction of borane 5 with dichlorocarbene gave dihydrophosphole-dichloromethylborane 6 and tetrahydro derivative 7a as the main products, and dichlorocyclopropane 8 as the minor component. Dichlorocarbene addition reaction of boranes 10 did not afford the corresponding phosphabicyclohexanes, but the dichloromethylborane complexes of the dihydro-and tetrahydrophospholes (11 and 7 respectively). Phosphabicyclohexane-borane 13 was synthesized from P-oxide 12 by change in the functionality. The dihydrophosphinine-boranes (16) were prepared by cyclopropane ring opening of phosphabicyclohexane 13, or by change in the functionality of P-oxide 15. Reaction of dihydrophosphinine-boranes 17 with dichlorocarbene gave traces of dihydrophosphinine-dichloromethylborane 18 instead of the phosphepine. The phosphepine-borane (20) was synthesised from oxide 19. The preparation of unsaturated phosphine-boranes was complicated by reduction side-reactions. The products were characterized by 31P, 11B, 1H and 13C NMR, as well as MS data.

Original languageEnglish
Pages (from-to)139-145
Number of pages7
JournalJournal of Organometallic Chemistry
Volume516
Issue number1-2
Publication statusPublished - Jun 14 1996

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phosphine
Boranes
boranes
phosphines
Oxides
synthesis
Addition reactions
oxides
Nuclear magnetic resonance
Derivatives
cyclopropane
products

Keywords

  • Dichlorocarbene
  • Dihydro-1H-phosphole
  • Dihydrophosphinine
  • Phosphabicyclohexane
  • Phosphepine
  • Phosphine-borane complex

ASJC Scopus subject areas

  • Biochemistry
  • Inorganic Chemistry
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Materials Chemistry

Cite this

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title = "Synthesis of phosphine-borane complexes of P-heterocycles",
abstract = "Dihydro-1H-phosphole-boranes 5 and 10 were prepared from phosphine oxides 1 and 9 respectively. Reaction of borane 5 with dichlorocarbene gave dihydrophosphole-dichloromethylborane 6 and tetrahydro derivative 7a as the main products, and dichlorocyclopropane 8 as the minor component. Dichlorocarbene addition reaction of boranes 10 did not afford the corresponding phosphabicyclohexanes, but the dichloromethylborane complexes of the dihydro-and tetrahydrophospholes (11 and 7 respectively). Phosphabicyclohexane-borane 13 was synthesized from P-oxide 12 by change in the functionality. The dihydrophosphinine-boranes (16) were prepared by cyclopropane ring opening of phosphabicyclohexane 13, or by change in the functionality of P-oxide 15. Reaction of dihydrophosphinine-boranes 17 with dichlorocarbene gave traces of dihydrophosphinine-dichloromethylborane 18 instead of the phosphepine. The phosphepine-borane (20) was synthesised from oxide 19. The preparation of unsaturated phosphine-boranes was complicated by reduction side-reactions. The products were characterized by 31P, 11B, 1H and 13C NMR, as well as MS data.",
keywords = "Dichlorocarbene, Dihydro-1H-phosphole, Dihydrophosphinine, Phosphabicyclohexane, Phosphepine, Phosphine-borane complex",
author = "G. Keglevich and K. {\'U}jsz{\'a}szy and A. Sz{\"o}ll{\"o}sy and K. Lud{\'a}nyi and L. Tőke",
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journal = "Journal of Organometallic Chemistry",
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TY - JOUR

T1 - Synthesis of phosphine-borane complexes of P-heterocycles

AU - Keglevich, G.

AU - Újszászy, K.

AU - Szöllösy, A.

AU - Ludányi, K.

AU - Tőke, L.

PY - 1996/6/14

Y1 - 1996/6/14

N2 - Dihydro-1H-phosphole-boranes 5 and 10 were prepared from phosphine oxides 1 and 9 respectively. Reaction of borane 5 with dichlorocarbene gave dihydrophosphole-dichloromethylborane 6 and tetrahydro derivative 7a as the main products, and dichlorocyclopropane 8 as the minor component. Dichlorocarbene addition reaction of boranes 10 did not afford the corresponding phosphabicyclohexanes, but the dichloromethylborane complexes of the dihydro-and tetrahydrophospholes (11 and 7 respectively). Phosphabicyclohexane-borane 13 was synthesized from P-oxide 12 by change in the functionality. The dihydrophosphinine-boranes (16) were prepared by cyclopropane ring opening of phosphabicyclohexane 13, or by change in the functionality of P-oxide 15. Reaction of dihydrophosphinine-boranes 17 with dichlorocarbene gave traces of dihydrophosphinine-dichloromethylborane 18 instead of the phosphepine. The phosphepine-borane (20) was synthesised from oxide 19. The preparation of unsaturated phosphine-boranes was complicated by reduction side-reactions. The products were characterized by 31P, 11B, 1H and 13C NMR, as well as MS data.

AB - Dihydro-1H-phosphole-boranes 5 and 10 were prepared from phosphine oxides 1 and 9 respectively. Reaction of borane 5 with dichlorocarbene gave dihydrophosphole-dichloromethylborane 6 and tetrahydro derivative 7a as the main products, and dichlorocyclopropane 8 as the minor component. Dichlorocarbene addition reaction of boranes 10 did not afford the corresponding phosphabicyclohexanes, but the dichloromethylborane complexes of the dihydro-and tetrahydrophospholes (11 and 7 respectively). Phosphabicyclohexane-borane 13 was synthesized from P-oxide 12 by change in the functionality. The dihydrophosphinine-boranes (16) were prepared by cyclopropane ring opening of phosphabicyclohexane 13, or by change in the functionality of P-oxide 15. Reaction of dihydrophosphinine-boranes 17 with dichlorocarbene gave traces of dihydrophosphinine-dichloromethylborane 18 instead of the phosphepine. The phosphepine-borane (20) was synthesised from oxide 19. The preparation of unsaturated phosphine-boranes was complicated by reduction side-reactions. The products were characterized by 31P, 11B, 1H and 13C NMR, as well as MS data.

KW - Dichlorocarbene

KW - Dihydro-1H-phosphole

KW - Dihydrophosphinine

KW - Phosphabicyclohexane

KW - Phosphepine

KW - Phosphine-borane complex

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