Sodium tetraphenylethylene

Tefranitromefhane, nitration with — 13, 401 1,7,10,15-Tefraoxadispiro-[5 2 5 2]hexadecane ring opening 12, 471 Tefraphenylboron salts of organic bases 14, 993 Tetraphenylethylene s. Sodium/ tetraphenylethylene Tefrasulfides... 

Other selected examples include tris(tetramethylethylene diamine-sodium)-9,9-dianthryl 143,154 alkali metal salts of 9,10-bis(diisopropylsilyl)anthracene 144,155 as well as the closely related naked 9,10-bis(trimethylsilyl)anthra-cene radical anion 145.156 This chemistry is further extended to the solvent-shared and solvent-separated alkali metal salts of perylene radical anions and dianions 146, 147,156 while other examples focus on alkali metal salts of 1,2-diphenylbenzene and tetraphenylethylene derivatives, where reduction with potassium in diglyme afforded contact molecules with extensive 7r-bonding, [l,2-Ph2C6H4K(diglyme)] 148.157 Extensive 7r-coordination is also observed in (1,1,4,4 tetraphenylbutadiene-2,3-diyl)tetracesiumbis(diglyme)bis(methoxyethanolate) 149.158... 

In the course of an extensive study of the mode of action of anionic catalysts, A. G. Evans used exclusively h.v.t. His investigation of the electron-transfer reactions involving 1,1,3,3-tetraphenylbutene-l, tetraphenylethylene and sodium naphthalide is of particular interest here because all the reaction mixtures were prepared by h.v.t. and both UV and ESR spectra were measured (J. E. Bennett et al, 1963). The paper contains full experimental details. 

Method. To 100 il of stomach contents or urine add 50 xl of M sodium hydroxide and extract with 100 xl of chloroform containing 10 xg/ml of tetraphenylethylene by the micro-extraction method, above inject 3 to 5 il of the chloroform extract on to both columns. 

Reduction of 308 with sodium borohydride gives 24% tetraphenylethylene with lithium borohydride, 75% of 2,2-diphenylethanol and 16% of 2,2-diphenylethyl disulfide with di-isobutylaluminum hydride, 39% l,l,3,3-tetraphenyl-2-propanone and 30% of benzophenone. Lithium aluminum hydride gives four products that may be formed by way of cyclopropanone intermediates. ... 

There have been few mechanistic studies of the one-electron reduction of ethylenes, but some conclusions have recently been drawn. Thus, the radicals formed from tetraphenylethylene and 1,1,3,3-tetraphenylbut-1-ene by the uptake of an electron (e.g. from sodium) are so sterically hindered that they do not dimerize but instead disproportionate to give the dianion and olefin (Bennett et al., 1964), e.g. 

Boekelheide and Phillips815 achieved the synthesis of the interesting /ra/ .r-15,16-dimethyldihydropyrene (17) and found that by all criteria, including both spectral properties and chemical reactivity, this hydrocarbon having substituents within the cavity of the (4n + 2) electron cloud is an aromatic molecule. In their synthesis, indicated briefly in the formulation, one meta link between two molecules of (8) is established by reaction with magnesium in the presence of ferric chloride to produce the bibenzyl derivative (9). Reaction of the diiodide (14) with finely divided sodium and tetraphenylethylene in tetrahydrofurane establishes the second meta link... 

Bromination of the olefin (617) gives the dibromide (618) with a rearranged carbon skeleton. The reaction may be reversed. Treatment of (618) with silver bromide gives the dibromide (619) with the original carbon skeleton, and dehalogenation of (619) with sodium and tetraphenylethylene regenerates the hydrocarbon. 

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