3-Phenylpropene oxide

As an example, the MIKE spectrum of the m/z 135 ion (MH ) of 3-phenylpropene oxide (measured under CI/tC4H9 conditions) [153] presents a base peak at m/z 117 (elimination of a water molecule) which is particularly wide, corresponding to energy release of about 440 meV. 

Phenylpropene oxide is selectively reduced in the presence of rra 5-stilbene oxide even with an excess amount of sodium borohydride (equation 16), and a similar system using lithium borohydride (LiBHa) also shows selective reduction of a styrene oxide in the presence of a benzamide. ... 

BaHe has also been employed to study the behavior of styrene oxide, o- and p-methylstyrene oxides, 1-phenylpropene oxide isomers, and 2-methyl-l-phenylpropene oxide. Styrene oxide yields mainly the primary alcohol. Phenyldimethyloxirane is transformed in accordance with Eq. 170. ... 

Lotter, J., Botes, A.L., van Dyk, M.S. and Breytenbach, J.C. (2004) Hydrolytic kinetic resolution of the enantiomers of the structural isomers trans-l-phenylpropene oxide and (2,3-epox5q)ropyl)benzene by yeast epoxide hydrolase. BiotechnoL Lett., 15,1197-1200. 

The oxidative coupling of alkenes which have two substituents at the 2 posi-tion, such as isobutylene, styrene, 2-phenylpropene, 1,1-diphenylethylene, and methyl methacrylate, takes place to give the 1,1,4.4-tetrasubstituted butadienes 285 by the action of Pd(OAc)2 or PdCF in the presence of sodium acetate[255-257]. Oxidation of styrene with Pd(OAc)2 produces 1.4-diphenylbutadiene (285, R = H) as a main product and a- and /3-acetoxystyrenes as minor pro-ducts[258]. Prolonged oxidation of the primary coupling product 285 (R = Me) of 2-phenylpropene with an excess of Pd(OAc)2 leads slowly to p-... 

Subtle ligand changes have pronounced effects in hydroboration of 1,1-disubstituted alkenes. Addition of HBcat across the C=C bond in 2,3,3-trimethyl-l-butene is catalyzed by [Rh(COD)Cl]2/DIOP at —5°C affording 2-t-butyl-l-propanol in 69% ee upon oxidation. In the case of 2-phenylpropene, [Rh(C2H4)2Cl]2 combines with either DIOP or BINAP to provide higher enantiomeric excesses than with [Rh(COD)Cl]2.46... 

Preliminary studies on catalytic osmylation were reported by Kokubo and co-workers who used bovine serum albumin, 0s04, and t-butylhydroperoxide as the oxidant. Turnover numbers up to 40 and an e.e. for 2-phenylpropene of 68% was achieved [23], Apparently the protein binds to osmium via nitrogen donors, but as different sites may be available this may lower the e.e. 

Lignans are secondary plant metabolites possessing a variety of biological activities [1,2]. They are dimers of phenylpropenes, which are by definition connected between C(8) and C(8 ) [3]. Lignans are of great structural variety due to numerous potential oxidation states at the C(7)/C(7 ) and C(9)/C(9 ) positions, and to the possibility of aryl-aryl bond formation [1-3]. 

For a better comparison of the different chiral reagents shown in Figure 2, the methoxyselenenylation of (it)-l-phenylpropene leading to addition products 42 is shown as a representative example in Table 1. After oxidative elimination, ether 43 can be obtained the absolute configuration of 43 is given in Table 1 as well (Scheme 7). 

The stereochemistry of hydrogenolysis of optically active 2-methyl-2-phenylaziridine (57, X = H) has been studied by Mitsui and Sugi.124,125 The products were mostly 2-phenyl-l-propylamine (58, X = H)) (92-100%), along with small amounts of 2-phenyl-2-propylamine or 2-cyclohexypropylamine (0-7%) and hydrocarbons (2-phenylpropene or -propane) (-0-5%). Over Pd(OH)2 in ethanol, the configuration of 58 (X = H) was predominantly of inversion, while over platinum oxide it was largely retained. With addition of NaOH to palladium, however, the retained product... 

Tanaka H, Ishihara M, Ichino K, Ito K (1988) Synthesis of Natural Coumarinolignans Oxidative Coupling of 7,8-Dihydroxycoumarins and Phenylpropenes in the Presence of Diphenyl Selenoxide. Heterocycles 27 2651... 

Terminal alkenes are oxidized with negligible rearrangement to give the 3-acyloxy species. - However, oxidation of internal alkenes, including cycloalkenes, may result in substantial or exclusive rearrangement. Most notable is the reaction of 1-phenylpropene exclusively to give 3-acetoxy-3-phenylpropene, in which deconjugation of the double bond t es place (equation 20). ... 

There is one direct method of preparing primary diamines from alkoies, in which the alkene is treated with nitric oxide and a cobalt complex, and the intermediate worked up reductively. The two-stage reduction gives better stereoselectivity (Scheme 38). Typical yields from alkenes listed and cisurans se-lectivities (expected product first) are cyclopentene, 70%, 70 30 rr[Pg.484]

Over-oxidation occurs if the solution is permitted to become basic. For example, 3-phenylpropene gives igjproximately equal amounts of phenylacetic acid and benzoic acid when oxidiz under phase transfer conditions using a two-phase benzene/water solvent system. However, when acetic acid is added, the yield of phenylacetic acid increases to 80%. ... 

The stereochemistry of the cyclohexene adduct was established as cis by comparison of the product with the authentic tnms-isomcr prepared by ring opening of cyclohexene oxide with tert-butylamine. Similarly, the products obtained from (Z)- and ( )-l-deuterio-l-decene were converted to diastereomeric oxazolidinones which were compared with the authentic diastereo-mers. Furthermore, different diastereomers were obtained from ( )- and (Z)-l-phenylpropene, It is therefore reasonable to assume complete syn addition for all alkenes. 

Hydroxyketones are versatile intermediates in the synthesis of pharmaceutical intermediates and heterocyclic molecules. a-Aryl hydroxyketones have been prepared by reaction of aryl aldehydes with 1,4-dioxane followed by reduction with lithium aluminum hydride (LAH) and by the selective LAH reduction of a-silyloxy a,P-unsaturated esters." WissneC has shown that treatment of acid chlorides with tris(trimethylsilyloxy)ethylene affords alkyl and aryl hydroxymethyl ketones. 1-Hydroxy-3-phenyl-2-propanone (3) has been generated by the osmium-catalyzed oxidation of phenylpropene and by the palladium-catalyzed rearrangement of phenyl epoxy alcohoP both in 62% yield. 

Numerous papers have been published describing the photochemical production of enones from carbonyl compounds and alkynes. The first detection of an oxetene intermediate involved low-temperature (-78 C) photolysis of 2-butyne and benzaldehyde to form the photoproduct (61), which was observed by NMR. llie oxetene undergoes further photoreaction with benzaldehyde to form the novel fused oxetane (62). Recently, Friedrich has reported Anther studies on the reactivity of oxetenes and developed alternative syntheses of the parent compound and 3-phenyloxete (64). The parent oxetene is found to have a themial half-life of approximately 8 h in solution at room temperature. The phenyl-substituted derivative (64) underwent slow ring-opening under acidic conditions to form 2-phenylpropenal and air oxidation to yield a formate derivative, probably via a radical process. 

PHENYLPROPENAL or 3-PHENYL-2-PROPENAL (104-55-2) Combustible liquid (flash point 231°F/111°C). A strong reducing agent. Contact with oxidizers, sodium hydroxide can cause fire and explosions. Incompatible with strong acids, strong bases, alkaline earth and alkali metals elevated temperatures will increase reaction. Attacks iron, aluminum, plastics, and coatings. 

Allene oxide-cyclopropanone systems. Treatment of the oxide of 3-chloro-2-triphenylsilyl-l-phenylpropene (1) leads to 3-elimination of (Ce H5 >3 SiF and... 

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