2- phenylpropene oxide, reaction

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). ... 

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. 

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. 

Oxidation of Alkenes and Other Unsaturated Hydrocarbons. The epoxidation of double bonds has been the major area for the application of DDO methodology and a wide range of alkenes are effectively converted to epoxides by solutions of DDO. Epoxidation is stereospecific with retention of afkene stereochemistry, as shown by the reactions of geometrical isomers for example, ( -1-phenylpropene gives the cw-epoxide cleanly (eq 2), whereas the (E) isomer yields the corresponding trans-epoxide. Rate studies indicate that this reagent is electrophilic in nature and that alkyl substitution on the double bond enhances reactivity Interestingly, cw-disubstituted alkenes react 7-9 times faster than the trans isomers, an observation that has been interpreted in terms of a spiro transition state. ... 

Pyrrolidinocyclohexene added drop wise at 0° under Ng (maintained throughout the reaction) during a few min. to a soln. of 2-nitro-l-phenylpropene in dry hexane, then allowed to warm to troom temp., and the product isolated after 2 hrs. -> 3-methyl-4-phenyl-8a-pyrrolidino-4a, 5,6,7,8,8a-hexahydro-4H-l, 2-benz-oxazine 2-oxide. Y 91%. F. e. s. A. T. Nielsen and T. G. Archibald, Tetrahedron 26, 3475 (1970). 

Remarkably, two successive CM reactions (R = (CH2)9CH3, R = Ph and vice versa) allowed the preparation of 118, whose vinyl group was subjected again to CM with 3-phenylpropene yielding a phosphine oxide with three different E-alkenyl groups. 

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