2-phenyl alkylate

Imidazole-4,5-dicarboxylic acids, coupling, 5, 403 decarboxylation, 5, 434 1-substituted synthesis, 5, 468 synthesis, 5, 362, 402, 484 Imidazole-4,5-dione, l-alkyl-2-phenyl-synthesis, 5, 129, 479 Imidazole-2,4-diones tautomerism, 5, 370 Imidazole-4,5-diones tautomerism, 5, 370 Imidazole-2,4-dithione, 5,5-diphenyl-tautomerism, 5, 370 Imidazole-2,4-dithiones tautomerism, 5, 370 Imidazolepropanol synthesis, 5, 486 Imidazoles accelerators epoxy resins, 1, 407... 

Thermal rearrangement of 2-vinylaziridine 203, with an electron-withdrawing substituent on the nitrogen atom, at reflux in decalin predominantly yielded 2-pyr-roline 204 along with some 3-pyrroline derivatives 205 (Scheme 2.50) [79]. A similar reaction was also observed with l-alkyl-2-phenyl-3-vinylaziridines 206 [80]. From these observations, the nature of the products formed depends on the natures of the substituents on the aziridine ring if the ring carbon carries a phenyl substituent, the thermolysis in most cases preferentially yields 2-pyrrolines. 

Reaction of the 2-phenyl-4-(phosphoranylidene)-5(47/)-oxazolone 219 with alkyl halides gives 4-alkyl-2-phenyl-5(47/)-oxazolones 220 in good yields. Reaction of 219 with acyl iodides or bromides gives C-4- or O-acyl products 221 or 222. Reaction of 219 with acyl chlorides gives 4-(l-chloroalkylidene)-2-phenyl-5(47/)-oxazolones 224 that are Wittig-like products. The use of benzoyl fluoride gives rise to 4-(l-benzoyloxybenzylidene)-2-phenyl-5(47/)-oxazolone 223. These reactions are summarized in Scheme 7.68. 

Alkyl-2-phenyl-5(4//)-oxazolones 342 react with the chloro-bridged iridium(III) complex [(t -C5Me5)IrCl2]2 to give cyclometalated mononuclear complexes 343. 

A number of systematic structural analyses have been described for families of saturated oxazolones. First, as mentioned previously, detailed smdies of NMR long-range coupling in 2,4-disubstimted-5(47/)-oxazolones and in 5(27/)-oxazo-lones have been reported." Similarly, detailed NMR studies of the kinetics of racemization of 2,4-disubstimted-5(47/)-oxazolones have been performed. A theoretical study of the spectral-luminescence properties of some 4-alkyl-2-phenyl-5(47/)-oxazolones has been reported and an investigation of the infrared (IR) and Raman spectra of 5(4//)-oxazolones, particularly of the carbonyl group vibration, has been reported. Electron impact mass spectra of saturated 5(47/)-oxazolones have been published. More recently this technique has been used to distinguish between the stereoisomers of some spirocyclopropane oxazolones 352 (Fig. 7.36). Finally, several studies of the HPLC behavior of 5(47/)-oxazolones complete a general view for this family of compounds. " " ... 

The l-[(l-alkyl-2-phenyl-2-cyclohexenyl)carbonyl]-2-methoxymethylpyrrolidines 4 can also be transformed into cyclohexadienyl ketones 5 with simultaneous removal of the auxiliary during hydrolytic workup29. 

The photoaddition of alkanes onto electron-poor alkynes (e.g., propiolate or acetilendicarboxylate esters) can be accomplished by a radical conjugate addition reaction [7]. Radicals have been generated either via hydrogen abstraction from cycloalkanes or via electron transfer from 2-alkyl-2-phenyl-l,3-dioxolanes. In the first case, the irradiation was pursued on an alkane solution of an aromatic ketone (used as the photomediator) and the alkyne. Under these conditions, methyl propiolate was alkylated upon irradiation in the presence of 4-trifluoromethylacetophenone to form acrylate 48 in 97% yield (E/Z= 1.3 1 Scheme 3.31) [78]. 

BMA - l-Benzyl-2-methylaziridine APOP - 3-Alkyl-2-phenyl-2-oxazolinium perchlorate... 

The IR spectra of 3-alkyl-2-phenyl-2//-l,3-oxazin-4-ones (17) exhibit a carbonyl band at 1650-1665 cm , and in the H NMR spectra the H-5 resonance appears as a singlet at about 5.3 ppm, with that of H-2 at 6.1-6.6 ppm <87CPB1860>. Both l,3-oxazine-4-thiones and l,3-oxazine-6-thiones are known and the crystal structures of several representative compounds including 6-(N,N-diethylamino)-5-methyl-2-phenyl-l,3-oxazine-4-thione (18) and 4-(A,A-diethylamino)-5-methyl-2-phenyl-l,3-oxazine-6-thione (19) have been determined by x-ray diffraction <86JCR(S)40>. 

The treatment of (Z)-3-aryl- and (Z)-3-alkyl-2-phenyl-3-nitropropenenitriles 126 (Fig. 35) gave access to 5-amino-3-aryl/alkyl-4-phenylisoxazoles 127 in good to moderate yields [165]. BY reduction of prochiral 7-nitroketones led to the enantioselective formation of (5) 4 nitroalcohols. Thus, 128b (Fig. 36) gave 130 in 74% yield with an e.e. of 99% [166]. Direduction was observed for the symmetrical diketone 128a that gave 58% of (2S,8S)-129 with an e.e. of 95% [167]. 

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