Photochemistry of functionalized diphosphiranes

Gouygou, Maryse; Tachon, C.; Koenig, Max; Dubourg, A.; Declercq, J.P.; Jaud, J.; Etemad‐Moghadam, Guita

doi:10.1021/jo00309a019

Cited by 32 publications

(26 citation statements)

References 4 publications

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“…The optimized value of the angle (0 = -77") corresponds quite well to the value given by X-ray structural analysis of 3c (0 = -72") (9). This preferential conformation in the solid state disappears when compounds 3a-f are in solution.…”

Section: Discussionsupporting

confidence: 80%

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Isomerism in the diphosphirane series

Fayet¹,

Mermillod-Blardet²,

Tachon³

et al. 1992

Can. J. Chem.

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The cisltrans stereochemistry of diphosphiranes la-g, 2a, and 2h is investigated by MNDO calculations in terms of substituent effects on intracyclic phosphorus and carbon atoms. This approach is completed by calculations of dipole moments. These results are compared to experimental dipole moment measurements of the synthesized diphosphiranes 3a-f, JEAN-PIERRE FAYET, DANIELE MERMILLOD-BLARDET, CHRISTINE TACHON, GUITA ETEMAD-MOGHADAM et MAX KOENIG.Can. J. Chem. 70, 2834 (1992).La stCrCochimie cisltrans des diphosphiranes la-g, 2a et 2h est CtudiCe en terme d'effets de substituants sur les atomes de carbone et de phosphore intracycliques. Cette approche, complCtCe par des calculs de moments dipolaires, est effectuCe par la mkthode MNDO. Ces rCsultats sont comparCs aux mesures experimentales de moments dipolaires de diphosphiranes 3a-f, synthCtisCes par ailleurs.

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Section: Discussionsupporting

confidence: 80%

“…The 3 '~{ '~) NMR spectra, reported as a singlet for 3a, 3c, and 3f and as an AB system for 3d, 3e, are consistent with a trans configuration. The X-ray analysis confirms this configuration (9).…”

Section: Resultssupporting

confidence: 63%

Isomerism in the diphosphirane series

Fayet¹,

Mermillod-Blardet²,

Tachon³

et al. 1992

Can. J. Chem.

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“…The first step of this reaction is probably the heterolytic rupture of the C-Cl bond inducing the subsequent preferential P-P bond rupture (Scheme 4). Contrary to the case of photochemical [3] to the more thermodynamically favorable phosphonium ion 7a occurs after the ring opening. Under similar conditions, the same final product 7a is obtained from 1,3-diphosphapropene 3a and AlC13 [5] (Scheme 4).…”

Section: Reaction With Aicimentioning

confidence: 79%

“…The bctionalized 1 ,3-diphosphapropenes 3a-b [3] and 4a-b [2] were prepared according to the previously described procedure, and diphosphapropene 15a was prepared by reaction of 3a with MeOH [3].…”

Section: Methodsmentioning

confidence: 99%

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Role of the conformation in the reactivity of 1,3‐diphosphapropenes

Gouygou

Koenig

Escudié

et al. 1991

Heteroatom Chemistry

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The symmetrical and unsymmetrical I ,3-diphosphapropenes 3 and 4 were obtained from the cowesponding diphosphiranes 1 and 2. The chemical behavior of these compounds has been studied. Phosphoniumphosphaalkenes 7a and 10a have been obtained in the reactions with aluminium trichloride. Whereas the symmetrical diphosphaallene 13 can be obtained by reaction of 1 or 3 with lithio compounds, the unsymmetrical diphosphaallene 14 cannot be prepared by a similar route. Reduction of 3a and 4a (obtained with a different conformation) by lithium aluminum hydride afforded phosphino-phosphaalkenes 17a and 18a (with a similar conformation); further dehydrochlorination with amines led to the symmetrical and unsymmetrical diphosphaallenes 13 and 14, respectively. The formation of allenes strongly depends on the conformation of the starting diphosphapropenes.

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Stable Radicals of the Heavy p‐Block Elements

Konu

Chivers

2010

Stable Radicals

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Photochemistry of functionalized diphosphiranes

Cited by 32 publications

References 4 publications

Isomerism in the diphosphirane series

Isomerism in the diphosphirane series

Role of the conformation in the reactivity of 1,3‐diphosphapropenes

Stable Radicals of the Heavy p‐Block Elements

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