4-Phenyl-l-hexene

This interpretation was supported by further investigations by GiacomelH and coworkers [73]. Racemic 4-phenyl-l-hexene was kineticaUy resolved by isomerization of the double bond using a catalyst system consisting of Al Buj, (R)-N,N-di-methyl-l-phenylethylamine and Ni(mesal)2. Very poor enantioselectivities (ee < 0.3%) were observed for both the isomerization product and the unreacted alkene. The authors note that it is essential to first react the alane with the chiral amine. No... 

Mit dem gleichen Reagenz erhalt man z. B. aus N-Propyl-benzaldimin erythro-4-Methyl-5-phenyl-5-propylamino-l-penten (75%) und aus N-Benzyl-benzaldimin 5-Benzylamino-4-methyl-5-phenyl-1-penten (90% erythro threo = 8 92)2 analog erhalt man aus 2-Phenyl-propanal-isopropylimin mit 9-Allyl-9-bora-bicyclo[3.3.1]nonan erythro-4-Isopropylamino-5-phenyl-l-hexen ( 90%)1. 

Predict the regioselectivity in the Diels-Alder reactions of acrolein and N-acetyl-2-cyano-4-phenyl-l-azabutadiene with 1-hexene, styrene, ethyl vinyl ether and methyl acrylate. The FOs of the azadiene are given below the others may be found in the Appendix. 

Problem 12.49. Draw structural formulas of the following compounds (a) 5-chloro-2,4-dimethyl-4-phenyl-2-hexene, (b) l-bromo-4-/-butylbenzene. 

To a 0.9 mL THF solution containing 4.3 mg Pd(OAc)2 (0.02 mmol, 10 mol %), tri-2-furylphosphine (5.1 mg, 0.02 mmol, 10 mol %), 32.7 mg triethylamine (0.32 mmol), and 75.2 mg 4-iodobenzoic acid ethyl ester (0.27 mmol), was added 65.7 mg (2-pyridyl)-l-hexenyl-dimethylsilane (0.30 mmol) under argon the reaction mixture was stirred at 60°C for 3 h. After the mixture was cooled to room temperature, 48.2 mg 4-iodoacetophenone (0.20 mmol) and 0.46 mL 1 M TBAF solution in THF were added to the reaction mixture, and this reaction mixture was stirred at 60°C for 14 h. The catalyst was removed by filtration through a short silica gel pad (EtOAc). The filtrate was evaporated, and the residue was chromatographed on silica gel (hexane/EtOAc, 10/1) to afford 48.6 mg ( )-l-(4-acetyl)phenyl-2-(4-ethoxycarbonyl)phenyl-l-hexene as a colorless oil, in a yield of71%. 

Draw the same reactions shown for 1, 3, 5, and 7 but use pheny-lacetic acid (2-phenylethanoic acid), 4,4-diphenylbutanal, 2-iodo-hexane, and 2-phenyl-l-hexene, respectively. In each case give the new product. 

Ciardelli et al [170] obtained similar results with stereoregular homo- or copolymerization with 4-methyl-1-pentene, of OA phenyl-a-olefins such as (/ )-4-phenyl-a-hexene (LXVIa) and ( S )-5-phenyl-l-heptene (LXVIb) in the presence of TiCls or VCI4/aluminum triisobutyl catalyst which is known for not producing any racemization. 

The intramolecular formal [3+3] cycloaddition reaction of l- [l-phenyl-2-(4-oxobut-2-enyloxy)ethyl]amino cyclo-hexen-3-one at 150°C in the presence of piperidinium acetate afforded /ra 3--l,4a-77-l-phenyl-l,2,4,4a,7,8,9,10-octahydro[l,4]oxazino[4,3- ]quinolin-7-one <2002JA10435>. At 85°C, the 6-(l-piperidnyl)-l,2,4,4a,5,6,7,8,9,10-dec-ahydro derivative formed, which could be converted into the l,2,4,4a,7,8,9,10-octahydro derivative by heating at 150 °C. Cyclization of iV-[(2-butyl-2-oxoethoxy)acetyl]-3,4-dimethoxyphenylethylamine on the action of TFA gave llb-butyl-1,3,4,6,7,1 lb-hexahydro[l,4]oxazino[3,4- ]isoquinolin-4-one <1997JOC2080>. 

Intramolecular secondary aminostyrenes 95-97 were also studied100. iV-2,2-Trimethyl-3-phenyl-3-buten-l-amine 95 was irradiated to obtain the elimination product 98 (equation 29). Irradiation of Af-methyl-4-phenyM-penten-l-amine 96 results in a single product 99 in 80% yield by GC analysis (equation 30). Similarily, irradiation of iV-methyl-5-phenyl-5-hexen-l -amine 97 results in the formation of a single product 100 in 70% yield (equation 31). The photochemistry of the (aminopropyl) indene 101 is also similar (equation 32). 

Ethyl-5-phenyl-2,4,6(l//,3//,5//)-pyrimidinetrione synonym 5-ethyl-5-phenylbarbituric acid. 5-Ethyl-1-methyl-5-phenylbarbituric acid. 5-Ethyl-5-phenyldihydro-2-thioxo-4,6(lEf,5H)-pyrimidine-dione synonym 5-ethyl-5-phenyl-2-thiobarbituric acid. 5-Ethyl-5-hexyl-2-thiobarbituric acid. 5-Ethyl-5-isopentylbarbituric acid. 5-Ethyl-5-(l-methylbutyl)-2-thiobarbituric acid. 5-(l-Cyclo-hexen-l-yl)-l,5-dimethylbarbituric acid. 5-Ethyl-5-(l-methylbutyl)barbituric acid. 5-(l-Cyclohexen-l-yl)-5-ethylbarbituric acid. 

Weitere Beispiele fur diese Art der Mitsunobu-Reaktion sind die Umwandlung eines 2,2-Diaryl-ethanols in 2-Amino-I-(4-benzyloxy-phenyl)-l-(2-benzyloxy-3-methoxy-phenyl)-ethan2 und die Umwandlung von 5-Hydroxy-2-methyl-l-hexen-3-in in 5-Phthalimido-2-methyl-l-hexen-3-in, das (wie oben formuliert) in 5-Amino-4-ethyl-l-hydroxy-2-methyl-2,3-hexadien ubergefuhrt werden kann3 ... 

The hydroformylation of several olefins in the presence of Co2(CO)8 under high carbon monoxide pressure is reported. (S)-5-Methylheptanal (75%) and (S)-3-ethylhexanal (4.8%) were products from (- -)(S)-4-methyl-2-hexene with optical yields of 94 and 72%, respectively. The main products from ( -)(8)-2,2,5-trimethyl-3-heptene were (S)-3-ethyl-6,6-di-methylheptanal (56.6%) and (R)-4,7,7-trimethyloctanal (41.2%) obtained with optical yields of 74 and 62%, respectively. (R)(S)-3-Ethyl-6,6-dimethylheptanal (3.5% ) and (R)(S)-4,7,7-trimethyloctanal (93.5%) were formed from (R)(S)-3,6,6-trimethyl-l-heptene. (+/S)-l-Phenyl-3-methyl-1-pentene, under oxo conditions, was almost completely hydrogenated to (- -)(S)-l-phenyl-3-methylpentane with 100% optical yield. 3-(Methyl-d3)-l-butene-4-d3 gave 4-(methyl-d3)pentarwl-5-d3 (92%), 2-methyl-3-(methyl-d3)-butanal-4-d3 (3.7%), 3-(methyl-d3)pentanal-2-d2,3-d1 (4.3%) with practically 100% retention of deuterium. The reaction mechanism is discussed on the basis of these results. 

Some of the bicyclo[3.1.0]hexene zirconocene derivatives, especially those containing a phenyl group, rearrange quantitatively to the corresponding 4-vinyl-l-metalla-2-cyclobutene derivatives when heated in toluene to 60-80 °C for several hours (equation 131). The 6,6-dimethyl-2,3-diphenyl-2-zirconabicyclo[3.1.0]hex-3-ene derivative prefers ring-opening to the isomeric j/. -allylic complex upon thermolysis. 

A high-yielding method for the synthesis of 2,3-dihydrofurans is provided by a ruthenium-catalyzed oxidative cyclization of 4-penten-l-ols (Equation 42). Treatment of 2-phenyl-5-hexen-2-ol gave the corresponding oxidative cyclization product, 2,5-dimethyl-2-phenyl-2,3-dihydrofuran, in quantitative yield <2003CL24>. 

Hexen 5-an -Nitro-4-phenyl- E14b, 793 (En-N02 + R-Si) Hydroxvlamin O-Benzoyl-N-cyclo-pentyl- X/l, 1232f. 

On the other hand, higher 1,2-asymmetric induction is observed for the cyclization of 5-aIkenols which bear an oxygenated function at C-4. Thus, treatment of 5-hexen-1,4-dioI (3) with phenyl-selenyl triflate in dichloromcthanc at —78 °C gives the corresponding tetrahydro-2/f-pyran 4 in 52% yield as a 91 9 (cis/trans) mixture. The preferential 2,3-cis relationship can be explained by analogy with the halocyclization of 4-pentene-l,3-diols (see Section 4.6.2.1.1.3.)19. 

By contrast, the selcnium-induccd cyclization of -V-substituted l-amino-4-hydroxy-5-hexenes 4 occurred with moderate to good diastereoselectivity, leading to mixtures of 3-hydroxy-2-phenyl-selenomethylpiperidine derivatives 5 in which the // arcs-isomer was the major component. The... 

The reductive dehalogenation of dichlorosilane 73 with magnesium in the presence of 1-hexene yields the corresponding l-[2-(dimethylaminomethyl)phenyl]-l-[2,4,6-tris(isopropyl)phenyl]-2- -butyl-l-silacyclopropane 74 (see Scheme 19) <1998CEJ852>. 

Methylation of l - azabicycl(i. U(I ltex-i-enes. The 1,3-di-azabicyclo[3.I.(Jlhex-ene-3 (1) is selectively methylated by trimethyloxonium fluoroborate to form 2,2,3-trimethyl-4-phenyl-6-/i-nitrophenyl-l-aza-3-azoniabieyclo[3.I.0]hexene-3 teirafluoro-borate (2) in 93% yield. Reaction of (1) with /n-chloroperbenzoic acid (1, I35-I39 ... 

The phenyl tellurium tribromide can be prepared in situ from diphenyl ditellurium and bromine. Olefins thus far investigated include isobutene, (E)- and (Z) -butene, 1 -hexene, 2-methyl-l-pentene, 1-octene, (E)- and (Z)-4-octene, 1-decene, phenylethene, 1-phenyl-l-methylethene, cyclopentene, cyclohexene, cycloheptene, and cyclooctene. Most of the reactions were carried out with phenyl tellurium tribromide in methanol. 

Trimethylaluminum reacted with l-(2-phenylcyclopropyl)ethylacetate (3) to give trans-5-phenyl-2-hexene (4) in 86% yield. Similar results were obtained with other trialkylaluminum reagents. The first step presumably involves electrophilic attack of the aluminum at oxygen. 

Wittig reagent, for preparation of 1,4-di-phenyl-l,3-butadiene, 40, 36 for preparation of methylenecyclo-hexene, 40, 66... 

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