Facile synthesis of 1, 2, 3, 4, 5, 6- hexahydrophosphinine 1-oxides by the hydrogenation of 1, 2-dihydrophosphinine 1-oxides

G. Keglevich, A. Tungler, László Tóket

Research output: Article

14 Citations (Scopus)

Abstract

The hydrogenation of the dihydrophosphinine oxides obtained from 3-methyl- or 3, 5-dimethy1-1-alkoxy-2, 5-dihydro-1H-phosphole oxides on ring enlargement gives the diastereoisomers of new hexahydrophosphinine oxides. Conformational analysis of the 3-methyl-products suggests the equilibria to be strongly biased toward structures with an equatorial C-methyl substituent. In contrast, the predominant diastereoisomer of the 3, 5-dimethyl-product exists as an equilibrium of two conformers. A new P-chloro-hexahydrdophosphinine has also been prepared from the ethoxy-derivative which is useful in the synthesis of the amino-product. The hexahydrophosphinine oxides are characterized by 31P, l3C and 1H NMR and mass spectroscopic methods.

Original languageEnglish
Pages (from-to)219-227
Number of pages9
JournalPhosphorus, Sulfur and Silicon and Related Elements
Volume70
Issue number1-4
DOIs
Publication statusPublished - jan. 1 1992

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Hydrogenation
Oxides
Nuclear magnetic resonance
Derivatives

ASJC Scopus subject areas

  • Biochemistry
  • Inorganic Chemistry
  • Organic Chemistry

Cite this

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title = "Facile synthesis of 1, 2, 3, 4, 5, 6- hexahydrophosphinine 1-oxides by the hydrogenation of 1, 2-dihydrophosphinine 1-oxides",
abstract = "The hydrogenation of the dihydrophosphinine oxides obtained from 3-methyl- or 3, 5-dimethy1-1-alkoxy-2, 5-dihydro-1H-phosphole oxides on ring enlargement gives the diastereoisomers of new hexahydrophosphinine oxides. Conformational analysis of the 3-methyl-products suggests the equilibria to be strongly biased toward structures with an equatorial C-methyl substituent. In contrast, the predominant diastereoisomer of the 3, 5-dimethyl-product exists as an equilibrium of two conformers. A new P-chloro-hexahydrdophosphinine has also been prepared from the ethoxy-derivative which is useful in the synthesis of the amino-product. The hexahydrophosphinine oxides are characterized by 31P, l3C and 1H NMR and mass spectroscopic methods.",
keywords = "Conformer, diastereoisomer, Dihydrophosphinine oxide, hexahydrophosphinine oxide, hydrogenation, stereospecific coupling",
author = "G. Keglevich and A. Tungler and L{\'a}szl{\'o} T{\'o}ket",
year = "1992",
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language = "English",
volume = "70",
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TY - JOUR

T1 - Facile synthesis of 1, 2, 3, 4, 5, 6- hexahydrophosphinine 1-oxides by the hydrogenation of 1, 2-dihydrophosphinine 1-oxides

AU - Keglevich, G.

AU - Tungler, A.

AU - Tóket, László

PY - 1992/1/1

Y1 - 1992/1/1

N2 - The hydrogenation of the dihydrophosphinine oxides obtained from 3-methyl- or 3, 5-dimethy1-1-alkoxy-2, 5-dihydro-1H-phosphole oxides on ring enlargement gives the diastereoisomers of new hexahydrophosphinine oxides. Conformational analysis of the 3-methyl-products suggests the equilibria to be strongly biased toward structures with an equatorial C-methyl substituent. In contrast, the predominant diastereoisomer of the 3, 5-dimethyl-product exists as an equilibrium of two conformers. A new P-chloro-hexahydrdophosphinine has also been prepared from the ethoxy-derivative which is useful in the synthesis of the amino-product. The hexahydrophosphinine oxides are characterized by 31P, l3C and 1H NMR and mass spectroscopic methods.

AB - The hydrogenation of the dihydrophosphinine oxides obtained from 3-methyl- or 3, 5-dimethy1-1-alkoxy-2, 5-dihydro-1H-phosphole oxides on ring enlargement gives the diastereoisomers of new hexahydrophosphinine oxides. Conformational analysis of the 3-methyl-products suggests the equilibria to be strongly biased toward structures with an equatorial C-methyl substituent. In contrast, the predominant diastereoisomer of the 3, 5-dimethyl-product exists as an equilibrium of two conformers. A new P-chloro-hexahydrdophosphinine has also been prepared from the ethoxy-derivative which is useful in the synthesis of the amino-product. The hexahydrophosphinine oxides are characterized by 31P, l3C and 1H NMR and mass spectroscopic methods.

KW - Conformer

KW - diastereoisomer

KW - Dihydrophosphinine oxide

KW - hexahydrophosphinine oxide

KW - hydrogenation

KW - stereospecific coupling

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U2 - 10.1080/10426509208049170

DO - 10.1080/10426509208049170

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VL - 70

SP - 219

EP - 227

JO - Phosphorus, Sulfur and Silicon and the Related Elements

JF - Phosphorus, Sulfur and Silicon and the Related Elements

SN - 1042-6507

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