Propionaldehyde 2-phenyl

The glycidic esters are of interest primarily because upon hydrolysis aud decarboxylation they aflFord aldehydes (if ClCHjCOOEt is used) or ketones (if substituted chloroacetic esters- ClCHRCOOEt are employed) having a higher carbon content than the original aldehyde or ketone. Thus (I) gives o-phenyl-propionaldehyde or hydratropaldehyde (II) ... 

Azides can use enamines as dipolarophiles for ],3 cycloadditions to form triazolines. These azides can be formate ester azides (186), phenyl azides (187-195), arylsulfony] azides (191-193,196), or benzoylazides (197,198). For example, the reaction between phenyl azide (138) and the piperidine enamine of propionaldehyde (139) gives 1 -phenyl-4-methy l-5-( 1 -piperidino)-4,5-dihydro-l,2,3-triazole (140), exclusively, in a 53% yield (190). None of the isomeric l-phenyl-5-methyl product was formed. This indicates that the... 

Phenyl isocyanate, with ethyl hydrazine-carboxylate to give 4-phenyl-l-car-bethoxysemicarbazide,51,122 Phenylmercuric acetate, with methallyl alcohol to yield 2-methyl-3-phenyl-propionaldehyde, 51, 17 1-PHENYL-1,3-PENTADIYNE, 50, 97 1-PHENYL-1,4-PENTADIYNE. 50, 97 a-Phenylpentanal, from 2-benzyl-4,4,6-trimethyl-5,6-dihydro-l,3(4H)-... 

Boc- and Cbz-protective groups turned out to be not tolerable in this protocol as indicated by epimerization of Boc- or Cbz-protected a-amino aldehydes substrates (e.g., N-Boc-protected 2-amino-3-phenyl-propionaldehyde 70% yield/24h, antijsyn ratio 50 50, 20% ee with 186). 

Similarly, 3-phenyl propionaldehyde gave rise to a 1 1.5 endo/exo mixture of adducts 110 (R = CH2CH2Ph), derived solely from reaction of the awfi-dipole. In an analogous fashion, thiazolidine carboxylic acid (111) also underwent awfi-dipole specific cycloaddition, with A-phenyl maleimide, after initial condensation with... 

In the examples of reductions of XCH2CHO mentioned above, hydration occurs both as antecedent and interposed reactions. The change of the second reduction step with pH is similar to that observed for acetaldehyde, but not quantitatively identical. This indicates that the second dehydration step is preceded here by a proton transfer. The rate of the proton transfer involving the carbanion formed as a primary electrolysis product governs the height of the acetaldehyde wave 84, 85). In the reduction of cinnamaldehyde, where only the hydration is interposed between the reductions of cinnamaldehyde and of 3-phenyl-propionaldehyde 87), the pH-dependence of the more negative wave of cinnamaldehyde is quantitatively identical with the pH-dependence of... 

Scheme 5.19 The achiral phosphine and chiral binaphthol-derived Bronsted acid-catalyzed MBH reaction of cyclohexenone and 3-phenyl propionaldehyde.

Ketones and Aldehydes The R2C=0 and the RCH=0 carbon atoms absorb in a characteristic region. Acetone absorbs at 203.3 ppm, and acetaldehyde at 199.3 ppm. Alkyl substitution on the a-carbon causes a shift to the left of the C=0 absorption of 2-3 ppm until steric effects supervene. Replacement of the CH3 of acetone or acetaldehyde by a phenyl group causes a shift to the right of the C=0 absorption (acetophenone, 195.7 ppm benzaldehyde. 190.7 ppm) similarly, a,/3-unsaturation causes shifts to the right (acrolein, 192.1 ppm, compared with propionaldehyde, 201.5 ppm). Presumably, charge delocalization by the benzene ring or the double bond makes the carbonyl carbon less electron deficient. 

Acetyl chloride acephate, azaconazole, chlorfenvinphos, cyhalotrin, dimethomorph, dinoseb acetate, fenitropan, fluxofenim, furconazole, mefluidide, propiconazole Acetyl chloride (dichloro) see dichloro Acetyl chloride phenyl carbinol bromadiolone Acetylene aldrin, 2,4 DB Acetyl hydrazine metamitron Acetylide (sodium) pronamide Acetyl magnesiun bromide empenthrin Acetyl morpholine dimethomorph Acetyloxy propionaldehyde furmecyclox Acrolein 8 hydroxy quinoline sulfate Acrylic acid propaquizafop Acryloyl chloride propaquizafop Acrylonitrile fenpiclonil, fludioxonil, nipyraclofen Aldrin dieldrin, endrin... 

Propiolaldehyde, phenyl-, 25, 92 Propionaldehyde, /1-ethoxy-, diethyl acetal, 25,1... 

SYNS ALDEHYDE B CYCLAMAL FEMA No. 2743 p-ISOPROPYL-O-METHYLHYDROCINNAMIC ALDEHYDE p-ISOPROPYDa-METHYLPHENYLPROP-YL ALDEHATIE a-METHYL-p-ISOPROPYLHYDRO-CINNAMALDEHYDE 2-METHYD3-(p-ISOPROPYL-PHENYL)PROPIONALDEHYDE... 

An example of this method is given by the synthesis of brevicomin. The desired a-(phenylthio) ether (7) was made by Diels-Alder addition of phenyl vinyl sulfide and methyl vinyl ketone. Treatment of (7) with lithium l-(dimethylamino)naphthalenide, followed by trapping of the anion with propionaldehyde and ring closure to an acetal during the acidic work-up, afforded a mixture of endo and exo isomers of brevicomin (Scheme 36). 

P, N] The addition of the enamines derived from a-phenyl-propionaldehyde and chiral amines to methyl vinyl ketone was the subject of an early investigation by Yamada and co-workers (Scheme 12, Table 2). Three types of chiral amine were used. The first set (entries 1-17) were derived from proline (25, 26). Additionally, some diamines derived from proline (entries 18-23) (27) and alkylamine mimics of proline were later examined (entries 24-27) (28). 

---