Synthesis of amino derivatives of sulfur tetrafluoride and phosphorus pentafluoride by silicon-nitrogen bond cleavage reactions

Demitras, G. C.; MacDiarmid, Alan G.

doi:10.1021/ic50056a031

Cited by 55 publications

(11 citation statements)

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“…The 19F nmr spectrum at -50°s howed only a singlet for RfOH at 74.5 ppm. The spectrum, outside the aromatic proton region, was identical with that of an authentic sample of isobutylene.. (b) Tricyclopropylcarbinol (5). A solution of 5 (0.258 g, 1.70 mmol) in 2 ml of dry CDCla was added to excess 1 (1.28 g, 1.91 mmol) in 4 ml of CDCla at room temperature in an inert atmosphere box.…”

mentioning

confidence: 77%

“…Chem., 32, 2976 (1967). Hz, 3 F, CFS) and 71.0 ppm (q, J = 10.6 Hz, 3 F, CF3), , 2.80 (m, 1 H, bridgehead CETCHORf), 2.96 (m, 1 H, bridgehead C//CH2), 3.80 (m, 1 H, RfOCEI, shoulder on 3.82 peak), 5.75 (d of d, .3 = 5.7 Hz, .2 = 3.0,1 H, CH= C at Q), and 6.09 (d of d, ,s = 5.7 Hz, J3:i = 3.0, 1 H, C=CH at C3).16 The mass spectra of RfOCCIs and diphenyl sulfide obtained by glpc-mass spectrometry on 5% SE-30 on Chromosorb W (acid washed, DMCS) were identical with those of authentic samples. The mass spectrum of a glpc peak containing 22 and/or 23 shows peaks at m/e 336 ( •+), 267…”

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confidence: 99%

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Sulfuranes. VI. Reactions involving the alkoxy ligands of dialkoxydiarylsulfuranes. Formation of olefins and ethers

Arhart¹,

Martin²

1972

J. Am. Chem. Soc.

204

117

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The crystal structure for a diphenyldialkoxysulfurane, (C6H5)2S[OC(CF3)2C6H5]2, reveals an approximate trigonal bipyramidal geometry about sulfur, with a lone pair considered to occupy one equatorial position, the two phenyl ligands occupying the other two equatorial positions (C-S-O angles range from 86.4(2) to 91.2(2)°; the C-S-C angle is 104.4(3)°), and with the electronegative alkoxy ligands occupying apical positions (O-S-O angle is 175.1(2)°w ith the distortion from linearity in the direction of the equatorial phenyl rings). The S-0 bond lengths (1.889(4) and 1.916(4) Á) are approximately 0.2 Á longer than the sum of the covalent radii as would be expected from an S-O bond order less than unity. The crystals are triclinic, the space group is Pi, and there are two molecules in a unit cell of dimensions a = 10.026(3), b = 14.268(3), c = 10.802(3) Á, a = 109°5 0'(2'), ß = 92°5 2'(2'), and y = 95°2 0'(2')• The structure was solved by Patterson-heavy atom methods based on sulfur, and has been refined to a conventional R of 0.070 for 3364 nonzero reflections measured by counter methods. Some comparisons of the bonding scheme with those for tetracovalent sulfur compounds containing halogen ligands are made.

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confidence: 77%

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confidence: 99%

Sulfuranes. VI. Reactions involving the alkoxy ligands of dialkoxydiarylsulfuranes. Formation of olefins and ethers

Arhart¹,

Martin²

1972

J. Am. Chem. Soc.

204

117

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“…Dimethyl-and diethyl-aminotetrafluorophosphoranes have been obtained in this way 110 The fact that phosphorodifluoridous amides are able to add chlorine to form adducts, which can be converted by sulphur dioxide into phosphorodifluoridic amides, was first noted by Ivanova 15 . Later work has established that both chlorine and bromine, in a solvent at low temperatures, react with the amides R ?…”

Section: /"\ Pf 3 and Salts [Rnh 3 F[pf 6 ]~ Being Formedmentioning

confidence: 99%

Phosphorus Fluorides

Drozd¹

1970

Russ. Chem. Rev.

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Advances in the chemistry of compounds containing P-F bonds, published during the past three or four years, are surveyed. Methods of synthesising several novel and some previously known products containing phosphorus and fluorine are reported, together with their chemical properties and the results of structural investigations using optical spectroscopy, nuclear magnetic resonance spectroscopy, and electron diffraction. The Review covers recent investigations on the stereochemistry of fluorides of five-coordinated phosphorus, and also problems of the complexing power of P[lll] and P[V] fluorides, which have been widely studied during recent years. Progress in the chemistry of the phosphorus fluorides will help to solve such important and continuing problems as the degree of hybridisation and the nature of the phosphorus-substituent bond in five-coordinated phosphorus compounds, the mechanism of chemical reactions involving phosphorus compounds of various coordination numbers, the possibility and the character of interference between substituents, etc. A list of 188 references is given. CONTENTS

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“…N,N-Dialkylaminosulfur trifluorides are very popular and useful deoxofluorination reagents [1]. N,N-Dimethylaminosulfur trifluoride as the first representative of this group was reported in 1964 [2], and N,N-diethylaminosulfur trifluoride called as DAST (b.p. 30-32 C/3 mmHg) was prepared in 1970 [3].…”

Section: Introductionmentioning

confidence: 99%

Aminosulfur Trifluoride Deoxofluorination

2019

Fluorination

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Synthesis of amino derivatives of sulfur tetrafluoride and phosphorus pentafluoride by silicon-nitrogen bond cleavage reactions

Cited by 55 publications

References 0 publications

Sulfuranes. VI. Reactions involving the alkoxy ligands of dialkoxydiarylsulfuranes. Formation of olefins and ethers

Sulfuranes. VI. Reactions involving the alkoxy ligands of dialkoxydiarylsulfuranes. Formation of olefins and ethers

Phosphorus Fluorides

Aminosulfur Trifluoride Deoxofluorination

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