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

P Bhattacharyya; Alexandra Martha Zoya Slawin; John Derek Woollins

doi:10.1039/b008071n

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

P Bhattacharyya, Alexandra Martha Zoya Slawin, John Derek Woollins

Research output: Contribution to journal › Article › peer-review

Abstract

An X-ray crystallographic study of [PhP(Se)(mu -Se)](2) 1, the oxidation product of the homocycle (PhP)(5) with ten equivalents of selenium, revealed that the molecule is centrosymmetric with a planar central P-2(mu -Se)(2) core and trans disposition of exocyclic P=Se 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)Se-2 unit across the C=C 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 N=N bond and substitution of a bridging selenium atom in 1 by an NPh unit, giving the first crystallographically characterised selenaazadiphosphetane (P2SeN) ring.

Original language	English
Pages (from-to)	300-303
Number of pages	4
Journal	Journal of the Chemical Society, Dalton Transactions
DOIs	https://doi.org/10.1039/b008071n
Publication status	Published - 2001

Keywords

Heterocycles
Phosphorus
Selenium
X-ray diffraction
X-ray powder diffraction
DITHIADIPHOSPHETANE DISULFIDES

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@article{3e2044b884c846b1a32df71b8377cb39,

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

abstract = "An X-ray crystallographic study of [PhP(Se)(mu -Se)](2) 1, the oxidation product of the homocycle (PhP)(5) with ten equivalents of selenium, revealed that the molecule is centrosymmetric with a planar central P-2(mu -Se)(2) core and trans disposition of exocyclic P=Se 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)Se-2 unit across the C=C 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 N=N bond and substitution of a bridging selenium atom in 1 by an NPh unit, giving the first crystallographically characterised selenaazadiphosphetane (P2SeN) ring.",

keywords = "Heterocycles, Phosphorus, Selenium, X-ray diffraction, X-ray powder diffraction, DITHIADIPHOSPHETANE DISULFIDES",

author = "P Bhattacharyya and Slawin, \{Alexandra Martha Zoya\} and Woollins, \{John Derek\}",

year = "2001",

doi = "10.1039/b008071n",

language = "English",

pages = "300--303",

journal = "Journal of the Chemical Society, Dalton Transactions",

issn = "1472-7773",

publisher = "Royal Society of Chemistry",

}

TY - JOUR

T1 - Heterocycle formation using [PhP(Se)(m-Se)]2. The crystal structures of [PhP(Se)(m-Se)]2, PhP(Se)Se2(C7H10) and PhP(Se)(m-Se)(m-NPh)P(Se)Ph

AU - Bhattacharyya, P

AU - Slawin, Alexandra Martha Zoya

AU - Woollins, John Derek

PY - 2001

Y1 - 2001

N2 - An X-ray crystallographic study of [PhP(Se)(mu -Se)](2) 1, the oxidation product of the homocycle (PhP)(5) with ten equivalents of selenium, revealed that the molecule is centrosymmetric with a planar central P-2(mu -Se)(2) core and trans disposition of exocyclic P=Se 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)Se-2 unit across the C=C 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 N=N bond and substitution of a bridging selenium atom in 1 by an NPh unit, giving the first crystallographically characterised selenaazadiphosphetane (P2SeN) ring.

AB - An X-ray crystallographic study of [PhP(Se)(mu -Se)](2) 1, the oxidation product of the homocycle (PhP)(5) with ten equivalents of selenium, revealed that the molecule is centrosymmetric with a planar central P-2(mu -Se)(2) core and trans disposition of exocyclic P=Se 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)Se-2 unit across the C=C 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 N=N bond and substitution of a bridging selenium atom in 1 by an NPh unit, giving the first crystallographically characterised selenaazadiphosphetane (P2SeN) ring.

KW - Heterocycles

KW - Phosphorus

KW - Selenium

KW - X-ray diffraction

KW - X-ray powder diffraction

KW - DITHIADIPHOSPHETANE DISULFIDES

UR - https://www.scopus.com/pages/publications/0035819718

U2 - 10.1039/b008071n

DO - 10.1039/b008071n

M3 - Article

SN - 1472-7773

SP - 300

EP - 303

JO - Journal of the Chemical Society, Dalton Transactions

JF - Journal of the Chemical Society, Dalton Transactions

ER -