Cinnamyl chloride

Phenylallyl chloride (cinnamyl chloride) [E 18685-01-3 Z 39199-93-4] M 152.6, b 92-93"/3mm. Distd under vacuum three times from K2CO3. 

Trioxymethylene, condensation with nitromethane, 41, 67 Triphenylcinnamylphosphonium chloride, from triphenylphosphine and cinnamyl chloride, 40, 36... 

Direct alkylation of the appropriate aryl-ethanolamine is, of course, widely used as, for example, in treatment of ephedrine (13a) with ethyl iodide to give the adrenergic agent, etafedrine (13b), or with cinnamyl chloride to give the muscle relaxant, cinnamedrine (14).10 Likewise, alkylation... 

In total, 29 phosphorus-containing chiral ligands of various structures were screened under the optimized y-selective conditions, but most of them gave little or no chiral induction. The four ligands 38a-d, all derived from (—)-TADDOL, depicted in Fig. 8.4 gave ees in excess of 30% in the reaction between ethyl magnesium bromide and cinnamyl chloride. 

Fig. 8.4. Ligands 38 employed in allylic su bstitution reactions between cinnamyl chloride and ...

Naftifine Naftifine, (E)-N-methyl-N-(3-phenyl-2-propenyl)-1 -naphthalinmethanamine (35.3.1), is synthesized by alkylating N-methyl-(l-naphthylmethyl)-amine with cinnamyl chloride in the presence of sodium carbonate [38 3]. 

To make the transformation even more useful, different carbon electrophiles should be connected sequentially in a stepwise manner. For this purpose, a transition-metal-catalyzed cross-coupling reaction opened the way. As shown in Scheme 22, cinnamyl chloride is treated with bis(iodozincio)methane (3) in the presence of palladium catalyst with various phosphine ligands. Phosphine ligands, having an electron-withdrawing group, such as tris[3,5-bis(trifluoromethyl)phenyl]phosphine and tris(2-furanyl)phosphine, show excellent results47. 

The nickel catalyzed reaction of 9 with an allyl chloride also proceeds in an Sn2 manner Eq. (42). Nickel dichloride complexed with a bidentate ligand (e.g. l,2-bis(diphenylphosphino)ethane) effects a highly selective (>99%) SN2 reaction with cinnamyl chloride [29]. 

Allyl 2,2,2-lrifluoroethyl ethers 36 are obtained from the alkoxides and cinnamyl chloride (for 36a) or allyl bromide (for 36b).17 Claisen rearrangement of the vinyl ethers 37 is complete within one to several hours at 80 C to give a, -difluoro aldehyde 38a or ketone 38b. 

Homoallylic alcohols This combination generates a Sn(0) species, which is more effective than Sn-Al (12, 486) for diastereoselective reaction of cinnamyl chloride with aldehydes to form anri-homoallylic alcohols. 

Monosubstituted allenes afford predominantly 2-chloro-2-alkenes (equation 47),73 75,76,78 although 1-phenyl-l,2-propadiene forms exclusively cinnamyl chloride (equation 48).79... 

Methyl-(l-naphthylmethyl)amine hydrochloride Sodium carbonate Dimethylformamide Cinnamyl chloride... 

Compounds of type LXXIII cannot be made by the rearrangement of the 7-substituted allyl ethers, because these compounds yield LXXIV by inversion. a,7-Dimethylallyl bromide,16 7,7-dimethylallyl bromide,29 cinnamyl chloride,84 and phytyl bromide 86 (a vitamin K synthesis) have been used in C-alkylation procedures. The silver salt of 2-hydroxy-l,4-naphthoquinone is converted to a mixture of C-alkylation product and two isomeric ethers by treatment with allylic halides and benzyl halides. ... 

Farina has shown that the reaction of 129 with cinnamyl chloride in THF with Pd2(dba)3 and tri-(2-furyl)phosphine as precatalytic system, results in incomplete formation of the C-allylated 130a, the isomeric cinnamyl ether of 129 being also isolated (91JA9585). 

S 2 -Ally lotion of R n or RZnCl. Cinnamyl chloride reacts with a variety of organozinc reagents in the presence of this Cu(I) reagent (5 mole %) at 20° to give the SN2 -products of allylation. The regioselectivity is comparable to that of RCu-BF3 at -70°. 

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