2-Seleno-2-methoxy-5,5-dimethyl-1,3,2-dioxaphosphorinane

Grand, André; Martin, John D.; Robert, J. B.; Tordjman, I.

doi:10.1107/s0567740875007996

Cited by 19 publications

(15 citation statements)

References 1 publication

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“…When the axial substituent is bonded to the P atom by means of a nearly single bond the flattening of the ring increases and the dihedral angle of the chair in the phosphorus part of the ring decreases to 41.8-3.7 ° (Murayama & Kainosho, 1969;Rodgers, White & Verkade, 1971;Grand, Martin, Robert & Tordjman, 1975;Bartczak, Christensen, Kinas & Stec, 1976;Beineke, 1969;Silver & Rudman, 1972;Cameron, Gatdecki & KarolakWojciechowska, 1976;Cameron, KarolakWojciechowska & Zwierzak, 1977;Haque, Caughlan, Hargis & Bentrude, 1970;Bukowska-Strzy~ewska, Michalski, Mtotkowska & Skoweranda, 1976;Drew & Rodgers, 1972).…”

Section: Lixo--/'mentioning

confidence: 99%

Bis(5,5-dimethyl-2-oxo-1,3,2-dioxaphosphorinanyl) oxide

Bukowska-Strzyżewska¹,

Dobrowolska²

1978

Acta Crystallogr Sect B

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Abstract. C10H2007P2, orthorhombic, Pbca, a = 26.88 (2), b = 9.99 (1), c = 11.13 (1) ,~; V = 2988.8 A3; M r = 314.22; D x = 1.39, D m = 1.39 g cm-3; Z = 8; F(000) = 1328.0; 2(Cu Ka) = 1.5418 A; gr(Cu Ktt) ---0.6. The structure was solved by direct methods and refined by least-squares methods with anisotropic temperature factors to an R value of 0. 121 for 1179 observed reflections. The symmetry of the bicyclic molecules is C~. The conformation around the bridge bonds P-O-P is staggered. The two structurally independent dioxaphosphorinane rings have partially flattened chair conformations with the double-bonded O atom in an equatorial and the linking O atom in an axial position. An analysis of the causes of the flattening observed in the 1,3,2-dioxaphosphorinane rings was carried out and the structural results are compared with those for bis(5,5-dimethyl-2-oxo-l,3,2-dioxaphosphorinanyl) sulphide.

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Section: Lixo--/'mentioning

confidence: 99%

Bis(5,5-dimethyl-2-oxo-1,3,2-dioxaphosphorinanyl) oxide

Bukowska-Strzyżewska¹,

Dobrowolska²

1978

Acta Crystallogr Sect B

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“…Some evidence that ring pucker a t phosphorus in I1 occurs in relief of steric interaction between the ring oxygens and C ( 14) comes from the bond angle P(2)-C(ll)-C(l4) of 111.4'. At the same time the angles P(2)-C(ll)-C(E) and P(Z)-C(ll)-C(13) are 107.5', as though the whole tert-butyl group had tipped at the C(11) slightly toward S (15). The angle O(1)-or 0(3)-P(2)-C(ll), 104.6', is only slightly and hardly significantly increased over that of the methyl compound 19 of Table I11 ( An alternative source of ring pucker at phosphorus in I1 could be the axial 5-tert-butyl if the two tert-butyl groups interact sterically in intermolecular fashion.…”

Section: -Dioxaphosphorinanesmentioning

confidence: 93%

Effects of axial tert-butyl substituents on conformations and geometries of saturated six-membered rings. Crystal and molecular structures of trans-2-methoxy-2-oxo-5-tert-butyl- and cis-2,5-di-tert-butyl-2-thio-1,3,2-dioxaphosphorinane

Warrent¹,

Caughlan²,

Hargis³

et al. 1978

J. Org. Chem.

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T h e title compounds crystallize in the orthorhombic system, the 2-methoxy compound (I) in the space group Pnma, and the 2-tert-butyl material (11) in space group Pmcn. Lattice parameters are: (I) a = 6.123 (41, b = 10.02 ( l ) , c = 17.65 (1) A, z = 4: (11) a = 10.077 ( 3 ) , b = 10.662 (3), c = 12.703 (3) A, z = 4. Compounds I and I1 both havechair-form ring conformations with the 5-tert-butyl group axial in both. For I the methoxy on phosphorus is axial and the phosphoryl oxygen is equatorial. The 2-tert-butyl is equatorial in I1 with the thiophosphoryl sulfur axial. In comparison to the structures of a large number of other phosphoranes, these rings systems, especially 11, appear to be somewhat flattened about the C(5) end of the molecule. This apparently results from steric interactions involving the axial tert-butyl groups and the ring atoms C(4), O ( l j , and O ( 3 ) and hydrogens bonded thereto. Bond angle deformations within the 5-tert-butyl and a t its point of attachment to the ring also attest t o this fact. T h e phosphorus end of the ring associated with I1 is highly puckered. This property is shown to be a general one for lJ.2-dioxaphosphorinanes with double-bonded 0, S, or Se axial. For I1 the ring pucker is unusually large. Explanations based on nonbonded interactions of the 2-tert-butyl with ring oxygens O(1) and O ( 3 ) or across the ring with the axial

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“…II s'agit d'6tudes sur les oxo-2 dioxaphosphorinanes-l,3,2 (Corbridge, 1974;Khaikin & Vilkov, 1972;Silver & Rudman, 1972); les thiono-2 dioxaphosphorinanes-l,3,2 , les s616no-2 dioxaphosphorinanes-l,3,2 (Grand, Martin, Robert & Tordjman, 1975); ou sur des compos6s mixtes du type cyclophosphamides (Clardy, Mosbo & Verkade, 1974). Le nombre de ces ~tudes s'explique par l'int6r~t que pr6sentent les mol6cules de ce type pour la compr6-hension g6n6rale de la st6r6ochimie des d6riv6s organophosphor6s et leur r61e 6ventuel en chimioth6rapie (Fergusson, 1975).…”

Section: Introductionunclassified

Structure cristalline et moléculaire du méthyl-2 thiono-2 dithiaphosphorinane-1,3,2 et du chloro-2 thiono-2 dithiaphosphorinane-1,3,2

Grand¹,

Martin²,

Robert³

1976

Acta Crystallogr Sect B

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The crystal and molecular structure of 2-methyl-2-thiono-l,3,2-dithiaphosphorinane (I) and of 2-chloro-2-thiono-l,3,2-dithiaphosphorinane (II) has been determined from X-ray data by a direct method. In both cases, the unit cell is orthorhombic, space group Pbca, with a= 11.156 (3), b= 13.121 (2), c= 11.338 (3) A for (I) and a= 10.919 (3), b= 12-700 (16), c= 11.681 (1) A for (II). The two molecules have a chair conformation, with the P=S bond in the equatorial orientation. The flattening of the ring is smaller than in the corresponding 1,3,2-dioxaphosphorinanes.

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2-Seleno-2-methoxy-5,5-dimethyl-1,3,2-dioxaphosphorinane

Cited by 19 publications

References 1 publication

Bis(5,5-dimethyl-2-oxo-1,3,2-dioxaphosphorinanyl) oxide

Bis(5,5-dimethyl-2-oxo-1,3,2-dioxaphosphorinanyl) oxide

Effects of axial tert-butyl substituents on conformations and geometries of saturated six-membered rings. Crystal and molecular structures of trans-2-methoxy-2-oxo-5-tert-butyl- and cis-2,5-di-tert-butyl-2-thio-1,3,2-dioxaphosphorinane

Structure cristalline et moléculaire du méthyl-2 thiono-2 dithiaphosphorinane-1,3,2 et du chloro-2 thiono-2 dithiaphosphorinane-1,3,2

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