2- -3-phenylpropyl phenyl

Fig. 6. 270 MHz HMR spectra of the aliphatic part of (a) 50/50 (b) > 99/1 mixtures of methyl-phenyl(2-phenylpropyl)stannyltriphenylphosphinetricarbonylcobalt (76)A + (76)B 1S>. (taken from Ref.18> with permission)...

C3 7H3 qCo03PSn, (Methyl-phenyl-2-(phenylpropyl)tin)-tricarbonyl-tri-phenylphosphine-cobalt, 46B, 1282... 

Chemical Name 1-(3-hydroxy-3-phenylpropyl)-4-phenyl-4-piperidinecarboxylic acid ethyl ester hydrochloride... 

In the reaction of 88 with /(-phenethyl bromide, l-phenethyl-3-phenylpropyl methyl sulfoxide and bis-3-phenylpropyl sulfoxide, besides 3-phenylpropyl methyl sulfoxide are obtained118. Sulfoxides, bearing a /1-hydrogen to the sulfmyl function, give olefins upon thermolysis. Utilizing this reaction, Trost and Bridges120 alkylated benzyl phenyl sulfoxide, 3,4-methylenedioxybenzyl phenyl sulfoxide, phenylthiomethyl phenyl sulfoxide, phenylsulfinylmethyl phenyl sulfoxide and cyanomethyl phenyl sulfoxide with alkyl, allyl and benzyl halides and subjected these sulfoxides to thermolysis, obtaining olefins in one-pot processes. 

Phenyl-2-propenoic acid, e279 3-Phenyl-2-propen-l-ol, c282 3-Phenyl-2-propenoyl chloride, c280 3-Phenylpropyl alcohol, pi46 Phenyl propyl ketone, b619... 

Phenylpropyl mercaptan, pi44 Phenyl sulfide, d770 Phenyl sulfone, d771 Phenyl sulfonic acid, b23 Phenyl sulfoxide, d772 (Phenylthio)acetic acid, tl 57... 

The cycloadditions of 1-substituted 1,2-cyclohexadienes and among them their dimerization are of interest because of the position selectivity. Does the reaction occur at the substituted or the unsubstituted ethylene subunit For that question to be answered, 1-methyl- (74), 1-phenyl- (75), 1-cyclopropyl- (76), l-(3-phenylpropyl)-(77) and l-trimethylsilyl-l,2-cyclohexadiene (79) were generated from the corresponding 1-substituted 6,6-dibromobicyclo[3.1.0]hexanes with methyllithium. Several of these dibromides are thermolabile, which particularly applies to the phenyl (93) [76] and the cydopropyl derivative [70], In those cases, it is advisable or necessary to prepare the dibromide in situ, that is, the dibromocarbene is liberated from tetrabro-momethane with methyllithium at -60 °C in the presence of the respective cyclopen-tene. Without workup, from the thus formed 6,6-dibromobicyclo[3.1.0]hexane, the 1,2-cyclohexadiene is then generated by addition of methyllithium at -30°C. 

In the alkaloid synthesis, L-phenylalanine (Figure 30) provides to alkaloid the phenyl or phenylpropyl nucleus. These kinds of nuclei occur in cathionine, cathine, ephedrine, pseudoephedrine and norpseudoephedrine. Such alkaloids are found especially in many species of Ephedra. Natural alkaloid molecules from these plants have similar properties to synthetic compounds used as narcotics (e.g., amphetamine). 

L-tyrosine (Figure 31) is an aromatic amino acid (similar in comoound from L-phenylalanine) which also provides phenyl (Figures 30-31) and phenylpropyl... 

Tyrosine is an important precursor of alkaloids with the phenyl and phenylpropyl nuclei. There are four basic alkaloid pathways. 

These alkaloids have a phenyl or phenylpropyl nucleus. The group includes simple phenyl amine (tyramine, hordenine), catecholamine (dopamine, noradrenaline, adrenaline), simple tetrahydroisoquinoline (mescaline, anhalamine, anhalonine, anhalonidine), benzylisoquinoline (e.g., papaverine), phthalideiso-quinoline (e.g., noscapine), phenethylisoquinoline (autumnaline, floramultine and kreysigine), tetrahydroisoquinoline (emehne and cephaeline) and terpenoid tetrahydroisoquinoline (secologanin and ipecoside) alkaloids. 

Figure 63. Structural development of phenyl and phenylpropyl alkaloids.

Under alkaline conditions isolating lignin degradation products which are essentially of a phenyl.ethyl rather than a phenylpropyl nature is structurally important and requires a lignin structure by which the 7-carbon may be removed as a result of a 0-7 carbon-carbon cleavage reaction, either by direct alkaline hydrolysis or alkali-catalyzed hydrogenolysis. 

The 13 C NMR chemical shifts of the para carbon for various phenyl-substituted sp2-and sp-hybridized carbocations (Figure 15) indicate that the demand for rr-aryl delocalization of the positive charge for the -silyl-substituted vinyl cation 393 is lower compared with that in a-phenylethyl (78), a-methyl-a-phenylpropyl (397) and cumyl (292) cations150 153. The stabilizing effect of the /)-silyl group in 393 is comparable to that of the cyclopropyl substituent in 1-cyclopropylbenzyl cation (398). The para carbon shift in the /)-cr-silyl... 

Phenylpropyl mercaptan, pl41 Phenyl sulfide, d688 Phenyl sulfone, d689 Phenylsulfonic acid, b22 Phenyl sulfoxide, d690 (Phenylthio)acetic acid, tl60... 

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