Cyclobutenyl derivatives of phosphorus and sulfur

Cullen, William R.; Dawson, David S.; Dhaliwal, P. S.

doi:10.1139/v67-112

Cited by 11 publications

(4 citation statements)

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“…Experimental and spectroscopic data appear in Tables 2-4. In the infrared spectra, the carbon-carbon double bond stretch for the mono and bis vinyl products appeared between 1594 and 1585 cm À1 in agreement with literature data [19]. Electron impact mass spectra of all products showed a molecular ion.…”

Section: Reactions Of Thiolssupporting

confidence: 88%

“…Vinyl substitution products have been obtained from 1,2-dichlorodifluorocyclopropene and potassium thiocyanate [9] and alkenes E-G [10][11][12][13][14][15][16][17] and HFCB [18][19][20] with aromatic and aliphatic thiols. Several conclusions can be drawn: (a) sulfur nucleophiles are more reactive than nitrogen or oxygen nucleophiles, (b) vinyl substitution is preferred regardless of the nature of the sulfur nucleophile and base employed, and (c) double substitution with thiols is unusually facile.…”

Section: Introductionmentioning

confidence: 99%

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Fluoroalkene chemistry

Timperley

2004

Journal of Fluorine Chemistry

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Section: Reactions Of Thiolssupporting

confidence: 88%

Section: Introductionmentioning

confidence: 99%

Fluoroalkene chemistry

Timperley

2004

Journal of Fluorine Chemistry

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“…Preparations of the ligands ffos, fefos, and ffars have been previously reported. [3][4][5][6][7] The known complexes diphosFe(CO)3, diphosFe2-(CO)s, and diarsFe(CO)¡¡ were prepared by methods similar to those previously described.1•1'16'8 The preparations of the fluorocarbon complexes described below are selected from a number of related experiments8 and give the optimum conditions so far found for obtaining the particular compound. Spectroscopic data for the complexes are listed in Tables I-VI (a) ffosFe(CO)3.-Iron pentacarbonyl (4.4 g, 22.4 mmol), ffos (0.4 g, 0.81 mmol), and acetone (10 ml) were sealed under vacuum in a thick-walled Pyrex tube.…”

mentioning

confidence: 99%

Five-coordinate iron carbonyl complexes with fluorocarbon-bridged ligands

Cullen¹,

Harbourne²,

Liengme³

et al. 1969

Inorg. Chem.

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P(OCeH5)3] with iodine in dichloromethane was shown by infrared spectroscopy to afford a third product in addition to x-C5H6Fe(CO)2I and x-C6H6Fe(CO)LI; these three compounds were formed in approximately equal amounts. When this iodination was performed in benzene, however, the unknown product separated out while trace quantities of x-CsH5Fe(CO)2I and x-CóH5Fe(CO)LI remained in the benzene solution. The precipitate was shown to be ionic and characterization of the tetraphenylborate derivative showed it to be [x-C5H6Fe(CO)2L]B(CeH6)4. The neutral compounds x-C5H6Fe(CO)LI were identified by comparing their infrared spectra with the spectra of authentic samples previously synthesized from x-C6H6Fe(CO)2l.2SThe physical and spectroscopic data for the ionic complexes are given in the tables. Conductivity data and spectroscopic evidence show, respectively, these derivatives to be 1:1 electrolytes in acetone and diamagnetic. The infrared spectra of these compounds in solution contain two peaks corresponding to C-0 stretching modes; the frequencies decrease with the increase of the over-all ( -) donor ability of the phos-(28) A. L. du Preez, M.S. Thesis, University of Pretoria.Inorganic Chemistry phorus donor ligand as expected. The single cyclopentadienyl proton resonance in the nmr spectra of these ionic compounds is split into a doublet due to phosphorus-hydrogen coupling. The coupling constant could only be measured for the compounds containing the ligands P(C2H3)3 and P(0-f-CsH7)3.The formation of both ionic and neutral compounds in the iodination of the monosubstituted derivatives demonstrates that this reaction occurs by at least two mechanistic pathways, one involving a symmetric cleavage and the other an asymmetric cleavage of the dinuclear parent. A similar scheme has been proposed for the halogenation of [x-C6HóFe(CO)2]2 on the basis of the isolation of [x-C6H6Fe(CO)3 ]X and x-CsHjFe-(CO)2X (X = halogen) from the reaction mixture.29Acknowledgments.-The authors express their gratitude to Dr. K. G. R. Pachler, National Chemical Research Laboratory, CSIR, Pretoria, South Africa, for the measurement of the nmr spectra. A. L. du P. thanks the South African Council for Scientific and Industrial Research and the University of Pretoria for financial support.

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“…1, when n = 2 and X = F, only For personal use only. disubstitution has ever been obtained with diphenylphosphine (1, 1 1) (the product is known as f4fos) yet dimethylarsine gives monosubstitution at 25 OC and disubstitution at 150 OC (2,11).…”

Section: C9mentioning

confidence: 99%