Heterocycle formation using [PhP(Se)(μ-Se)]2. The crystal structures of [PhP(Se)(μ-Se)]2, PhP(Se)Se2(C7H10) and PhP(Se)(μ-Se)(μ-NPh)P(Se)Ph

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Abstract

An X-ray crystallographic study of [PhP(Se)(μ-Se)]21, the oxidation product of the homocycle (PhP)5 with ten equivalents of selenium, revealed that the molecule is centrosymmetric with a planar central P2(μ-Se)2 core and trans disposition of exocyclic PSe bonds. In the reaction of 1 with norbornene (bicyclo[2.2.1]hept-2-ene), crystallographic analysis of the product 2 revealed exo addition of a PhP(Se)Se2 unit across the CC bond, giving a 1,2-diselena-3-phospholane (C2PSe2) ring. Norbornadiene (bicyclo[2.2.1]hepta-2,5-diene) reacts more slowly with 1, allowing the isolation of a 1,2-selenaphosphetane (C2PSe ring) in addition to a diselenaphospholane. The reaction of 1 with azobenzene proceeds with cleavage of the NN bond and substitution of a bridging selenium atom in 1 by an NPh unit, giving the first crystallographically characterised selenaazadiphosphetane (P2SeN) ring.

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Autori: Pravat Bhattacharyya (University of St Andrews); Alexandra M. Z. Slawin iD (University of St Andrews); J. Derek Woollins iD (University of St Andrews)
Pubblicato in: Journal of the Chemical Society Dalton Transactions, n. 3, pp. 300-303
Data di pubblicazione:01/01/2001
Editore:Royal Society of Chemistry
Tipo di documento:Articolo
Lingua:inglese
DOI: 10.1039/b008071n
ISSN:1364-5447, 1472-7773
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Citazioni ricevute:39
Soggetti:
Organoselenium and organotellurium chemistry (Life Sciences > Pharmacology, Toxicology and Pharmaceutics > Toxicology)
Synthesis and characterization of novel inorganic/organometallic compounds (Physical Sciences > Chemistry > Inorganic Chemistry)
Organophosphorus compounds synthesis (Physical Sciences > Chemistry > Organic Chemistry)
heterocyclic synthesis, norbornene, norbornadiene, azobenzene, bridging selenium, crystal structure
Identificativi: OpenAlex W2131910359

Dati dell'indice centrale: OpenAlex (licenza CC0).

Riassunto:An X-ray crystallographic study of [PhP(Se)(μ-Se)]21, the oxidation product of the homocycle (PhP)5 with ten equivalents of selenium, revealed that the molecule is centrosymmetric with a planar central P2(μ-Se)2 core and trans disposition of exocyclic PSe bonds. In the reaction of 1 with norbornene (bicyclo[2.2.1]hept-2-ene), crystallographic analysis of the product 2 revealed exo addition of a PhP(Se)Se2 unit across the CC bond, giving a 1,2-diselena-3-phospholane (C2PSe2) ring. Norbornadiene (bicyclo[2.2.1]hepta-2,5-diene) reacts more slowly with 1, allowing the isolation of a 1,2-selenaphosphetane (C2PSe ring) in addition to a diselenaphospholane. The reaction of 1 with azobenzene proceeds with cleavage of the NN bond and substitution of a bridging selenium atom in 1 by an NPh unit, giving the first crystallographically characterised selenaazadiphosphetane (P2SeN) ring.
ISSN:1364-5447
1472-7773
DOI:10.1039/b008071n