Formation of 2,3‐dihydro‐1,3,2‐benzoxazaphospholes by cheletropic reaction of o‐quinone monoimines with triphenylphosphane. Crystal and molecular structures of 2,3‐dihydro‐2,2,2‐triphenylphenanthro[9,10‐d]‐1,3,2λ5‐oxazaphosphole and 5,7‐di‐tert‐butyl‐2,3‐dihydro‐2,2,2‐triphenyl‐1,3,2λ5‐benzoxazaphosphole

G. Speier, Zoltán Tyeklár, Vilmos Fülöp, L. Párkányí

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7 Citations (Scopus)

Abstract

9,10‐Phenanthrenequinone monoimine (1c) or 3,5‐di‐tert‐butyl‐o‐benzoquinone (2a) in the presence of ammonia undergo cycloaddition with triphenylphosphane to give 2,3‐dihydro‐1,3,2λ5‐benzoxazaphospholes (3) in good yields. 5,7‐Di‐tert‐butyl‐2,3‐dihydro‐2,2,2‐triphenyl‐1,3,2λ5‐benzoxazaphosphole (3a) shows a tautomeric equilibrium with the iminophosphorane 4a while 2,3‐dihydro‐2,2,2‐triphenylphenanthro[9,10‐d]‐1,3,2λ5‐oxazaphosphole (3c) has a cyclic structure in solution. Both compounds are cyclic in the solid form as confirmed by X‐ray structure diffraction studies.

Original languageEnglish
Pages (from-to)1685-1688
Number of pages4
JournalChemische Berichte
Volume121
Issue number9
DOIs
Publication statusPublished - 1988

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Cycloaddition
Ammonia
Molecular structure
Diffraction
Crystal structure

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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title = "Formation of 2,3‐dihydro‐1,3,2‐benzoxazaphospholes by cheletropic reaction of o‐quinone monoimines with triphenylphosphane. Crystal and molecular structures of 2,3‐dihydro‐2,2,2‐triphenylphenanthro[9,10‐d]‐1,3,2λ5‐oxazaphosphole and 5,7‐di‐tert‐butyl‐2,3‐dihydro‐2,2,2‐triphenyl‐1,3,2λ5‐benzoxazaphosphole",
abstract = "9,10‐Phenanthrenequinone monoimine (1c) or 3,5‐di‐tert‐butyl‐o‐benzoquinone (2a) in the presence of ammonia undergo cycloaddition with triphenylphosphane to give 2,3‐dihydro‐1,3,2λ5‐benzoxazaphospholes (3) in good yields. 5,7‐Di‐tert‐butyl‐2,3‐dihydro‐2,2,2‐triphenyl‐1,3,2λ5‐benzoxazaphosphole (3a) shows a tautomeric equilibrium with the iminophosphorane 4a while 2,3‐dihydro‐2,2,2‐triphenylphenanthro[9,10‐d]‐1,3,2λ5‐oxazaphosphole (3c) has a cyclic structure in solution. Both compounds are cyclic in the solid form as confirmed by X‐ray structure diffraction studies.",
author = "G. Speier and Zolt{\'a}n Tyekl{\'a}r and Vilmos F{\"u}l{\"o}p and L. P{\'a}rk{\'a}ny{\'i}",
year = "1988",
doi = "10.1002/cber.19881210923",
language = "English",
volume = "121",
pages = "1685--1688",
journal = "Chemische Berichte",
issn = "0009-2940",
publisher = "Wiley-VCH Verlag",
number = "9",

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TY - JOUR

T1 - Formation of 2,3‐dihydro‐1,3,2‐benzoxazaphospholes by cheletropic reaction of o‐quinone monoimines with triphenylphosphane. Crystal and molecular structures of 2,3‐dihydro‐2,2,2‐triphenylphenanthro[9,10‐d]‐1,3,2λ5‐oxazaphosphole and 5,7‐di‐tert‐butyl‐2,3‐dihydro‐2,2,2‐triphenyl‐1,3,2λ5‐benzoxazaphosphole

AU - Speier, G.

AU - Tyeklár, Zoltán

AU - Fülöp, Vilmos

AU - Párkányí, L.

PY - 1988

Y1 - 1988

N2 - 9,10‐Phenanthrenequinone monoimine (1c) or 3,5‐di‐tert‐butyl‐o‐benzoquinone (2a) in the presence of ammonia undergo cycloaddition with triphenylphosphane to give 2,3‐dihydro‐1,3,2λ5‐benzoxazaphospholes (3) in good yields. 5,7‐Di‐tert‐butyl‐2,3‐dihydro‐2,2,2‐triphenyl‐1,3,2λ5‐benzoxazaphosphole (3a) shows a tautomeric equilibrium with the iminophosphorane 4a while 2,3‐dihydro‐2,2,2‐triphenylphenanthro[9,10‐d]‐1,3,2λ5‐oxazaphosphole (3c) has a cyclic structure in solution. Both compounds are cyclic in the solid form as confirmed by X‐ray structure diffraction studies.

AB - 9,10‐Phenanthrenequinone monoimine (1c) or 3,5‐di‐tert‐butyl‐o‐benzoquinone (2a) in the presence of ammonia undergo cycloaddition with triphenylphosphane to give 2,3‐dihydro‐1,3,2λ5‐benzoxazaphospholes (3) in good yields. 5,7‐Di‐tert‐butyl‐2,3‐dihydro‐2,2,2‐triphenyl‐1,3,2λ5‐benzoxazaphosphole (3a) shows a tautomeric equilibrium with the iminophosphorane 4a while 2,3‐dihydro‐2,2,2‐triphenylphenanthro[9,10‐d]‐1,3,2λ5‐oxazaphosphole (3c) has a cyclic structure in solution. Both compounds are cyclic in the solid form as confirmed by X‐ray structure diffraction studies.

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