Dimethyl diphenylmethane

CnHaBr IlfO.S.e.Dibi om-t. difttbylamino-4-o -2.S.dimethyl-diphenylmethan-iod methylat IS, 718. 

H,gBrgIL0 3.6-DibRHB-2 -amnio.4 Hlr methy1aminO 4.oxy-2.6-dimethyl diphenylmethan 13II 432. 

Cj HgoNiO 4-Methylnitrosa Ulno-4 > methyl < anamino-2.2 -dimethyl-diphenylmethan 18 182. 

CuHgiBrjNOg 3.6-Dibrom-4 -diinethylamjiio-4-acetoxy-2.5-dimethyl-diphenylmethan... 

N.N -Di-p-tolyl-N.N -dicyan-penta mefchylendiamin 12, 978. 4.4. 4 "-Triammo-tribenzylamin 13,176. 4.4 -Bia- [inethyl-c3ruiinethyl-amino j-2.2 -dimethyl-diphenylmethan 13 I 82. 4.4 -Bia-[metbyl-oyanmethyl-amino]-2.3 dimethyl diphenylmethan 13 I 83. 4.6.4 6 X araamino-3.3 -d methyl-tripbenyl methan 13, 343. 

Oxidation of diphenylmethane in basic solutions involves a process where rate is limited by and equal to the rate of ionization of diphenylmethane. The diphenylmethide ion is trapped by oxygen more readily than it is protonated in dimethyl sulfoxide-text-butyl alcohol (4 to 1) solutions. Fluorene oxidizes by a process involving rapid and reversible ionization in text-butyl alcohol solutions. However, in the presence of m-trifluoromethylnitrobenzene, which readily accepts one electron from the carbanion, the rate of oxygen absorption can approach the rate of ionization. 9-Fluorenol oxidizes in basic solution by a process that appears to involve dianion or carbanion formation. Benzhydrol under similar conditions oxidizes to benzophenone by a process not involving carbanion or dianion formation. 

Table II. Calculated Ionization Rate Constants for Diphenylmethane in Dimethyl Sulfoxide (80% )— f erf-Butyl Alcohol Solutions...

Diphenylmethan- -dichlorid XII/1, 401 Diphenylmethan- -dicthylcstcr XII/1, 445 Dipheny]-(4-methoxy-phenyl)-methan- -dimethyl-ester E2, 379... 

Arnold s demonstration" that oxocarbenium ion intermediates can be formed through homobenzylic ether radical cation fragmentation reactions shows that mild oxidizing conditions can be used to prepare important reactive intermediates. Scheme 3.2 illustrates a critical observation in the development of an explanatory model that allows for the application of radical cation fragmentation reactions in complex molecule synthesis. In Arnold s seminal work, cleavage of the benzylic carbon-carbon bond in substrate 1 is promoted by 1,4-dicyanobenzene (DCB) with photoirradiation by a medium-pressure mercury vapor lamp. With methanol as the solvent, the resulting products were diphenylmethane (2) and formaldehyde dimethyl acetal (3). 

Similar pressure effects have been observed in the 1,3-dipolar cycloaddition of diazo-diphenylmethane to various alkenes. This is in agreement with a concerted mechanism involving an isopolar activated complex [752, 753] cf. Section 5.3.3. For the 1,3-dipolar cycloaddition of diazo-diphenylmethane to dimethyl acetylenedicarboxylate at 25 °C in n-hexane (AF = —24 cm mol ) and in acetonitrile (AF = —15 cm mol ), the solvent-induced difference AAF is only 9 cm mol this corresponds to a very small rate constant solvent effect, k2(CH3CN)/A 2(n-C6Hi4) = 3.4 [752]. 

DIFENHYDRAMIN DIFENIDRAMINA (ITALIAN) DIHIDRAL DIMEDROL DIMEDRYL fi-DIMETHYLAMINO-AETHYL-BENZHYDRYL-AETHER (GERMAN) P-DIMETHYLAMINOETHANOL DIPHENYLMETHYL ETHER a-(2-DIMETHYLAMINO-ETHOXY)DIPHENYLMETHANE P-DIMETHYL-AADNOETHYLBENZHYDRYLETHER DIPHANTINE... 

Auramine Auraminebose or Tetramethy -p,-diominoimino-benzophenone (called in Beil 4,4 -Bis-dimethyl amino-benzophenon), (CH,)jN-CsH4.C( NH)-CbH4-N(CH,)3, mw 267.36, N 15.72 %. Col Uts mp 136 insol in w sol in ale in eth. Can be prepd by treating its hydrochloride (see below) in aq ale with dil NaOH, as described in Ref 3, or by heating 4,4 -bis-dimethylamino-diphenylmethane with sulfur followed by treatment with ammonia (Retl, p 92)... 

The procedure can also be used to oxidize certain aromatic hydrocarbons (diphenylmethane - benzophenone, 48% yield), sulfides and sulfoxides to sul-fones (dimethyl sulfide — dimethyl sulfone, 100% yield). 

Pheayltoloxamine, N,N-Dimetkyl 2 [2-(pkenyl-nethyl)phenoxy]ethanamine N,N-dimethyl-2-ia-phenyt-o-ulyloxy)ethylamine AUV-dimethyl-2-( -phenyl-o-toloxy)-ethylamine 2-(2-dimethy]aminoethoxy)diphenylmethane ... 

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