2-Ethyl-2-propen

Scheme 2. Isomerisation of 2-ethyl propenal to trans-2-methyl-2-butenal.

CH3CH=CH2 + CH3CH2CH2OCH2CH3 Propene (9%) Ethyl propyl ether (91%)... 

Chemically, wood tar is a complex mixture that contains at least 200 individual compounds, among which the foUowing have been isolated (1) 2-methoxyphenol, 2-methoxy-4-ethylphenol, 5-meth5i-2-methoxyphenol, 2,6-x5ienol, butyric acid, crotonic acid, 1-hydroxy-2-propanone, butyrolactone, 2-methyl-3-hydroxy-4JT-pyran-4-one, 2-methyl-2-propenal, methyl ethyl ketone, methyl isopropyl ketone, methyl furyl ketone, and 2-hydroxy-3-methyl-2-cyclopenten-l-one. 

H,12H-Dibenz[67]azocin-6-one, 5-benzoyl-AG7AG+, 7, 705 <73JCS(P1)205) Dibenzo[e,g]benzothiazol-l-ium, l-ethyl-2-[A -(1 -ethyl-2 -dibenzo[e,g]benzothiazolylidene)-3-y lidene-1 -propen]-1 -yl-visible, I, 345 B-76MI11201)... 

Bromination of the methyl group of (249) with A -bromosuccinimide, followed by reaction with excess secondary amine gave (250) which shows combined analgesic and antitussive properties. The Reformatsky reaction has also been used for the preparation of 2-amino-ethyl 3,3-diaryl-3-hydroxypropanates (251) as well as their dehydration products. The propene amides (252) have also been prepared for pharmacological evaluation. In l-methyl-3-bis (2-thienyl)-... 

Alk = Et), a-methylstyrene (156, Ar = Ph), and allyl-benzene (160, Ar = Ph) are representatives of the four types of monosubstituted propenes (olefins 157 and 158, etc. written in Table I as equilibrium pairs undergo equilibration during the course of the reaction and yield the same pyrylium salt on diacylation). Disubstituted propenes which gave pyrylium salts on diacylation are 2-pentene (163, Alk = Me) and 1,2-diphenylpropene (164, Ar = ph),305 3-ethyl-2-pentene represents a trisubstituted propene... 

The irradiation of 2,5-dimethylfuran in the presence of mercury vapor gave a complex mixture of products. Carbon monoxide and propene were removed as gaseous products. Then, cis- and rran.s-l,3-pentadiene, isoprene, 1,3-dimethylcyclopropene, 2-pentyne, 2-ethyl-5-methylfuran, hexa-3,4-dien-2-one, 1-methyl-3-acetylcyclopropene, and 4-methylcyclopent-2-enone were obtained (Scheme 8) (68JA2720 70JA1824). The most abundantproduct was the cyclopentenone 19, the second was the 1,3-pentadiene 12, while the third product was the cyclopropenyl derivative 18. 

It was elaimed that eyelization of ethyl 2-ehloro-5-eyelopropyl-6- [(A-(4,5-dimethoxy-2-nitrophenyl)methoxy)earbonyl]-A-(2-fluoro-3-hydroxy-l-oxo-2-propen-l-yl)amino nieotinate (321) in boiling aqueous dioxane in the presenee of K2CO3 overnight yielded l- [(4,5-dimethoxy-2-nitrophe-nyl)methoxy]earbonyl -9-eyelopropyl-3-fluoro-2-oxo-2,6-dihydropyrido[l, 2-n]pyrimidine-7-earboxylate (160) (95MIP1, 96MIP4, 96USP5580872). 

Sodium N-(1-methoxycarbonyl-1 -propen-2-yl)-D(-)-0 -amino-(4-hydroxyphenyl)acetate Ethyl chlorocarbonate... 

The largest commercial process is the hydroformylation of propene, which yields n-butyraldehyde and isobutyraldehyde. n-Butyraldehyde (n-butanal) is either hydrogenated to n-butanol or transformed to 2-ethyl-hexanol via aldol condensation and subsequent hydrogenation. 2-Ethylhexanol is an important plasticizer for polyvinyl chloride. This reaction is noted in Chapter 8. 

The Wacker reaction can also be carried out for other olefins with terminal double bonds. With propene, for example, approximately 90% yield of acetone is obtained. 1-Butene gave approximately 80% yield of methyl ethyl ketone. 

The Diels-Alder cycloadclition reaction occurs most rapidly if the alkene component, or dienophile ("diene lover"), has an electron-withdrawing substituent group. Thus, ethylene itself reacts sluggishly, but propenal, ethyl propenoate, maleic anhydride, benzoquinone, propenenitrile, and similar compounds are highly reactive. Note also that alkynes, such as methyl propynoate, can act as Diels-Alder dienophiles. 

The (Z)-configuration of the enol ether however is a prerequisite for both high. yyn-selecting and high optical purity of the products23. When, on the other hand, (Z)-2-benzyloxy-l-ethyl-thio-l-trimethylsilyloxy-l-propene is allowed to react with 2-propional in the presence of the diamine 2, the anti-aldol product is obtained in 92% ee42. 

L PROLYLGLYCYLGLYCINE,At CARBO BEN ZOXY-3-HY DROXYETHYL ESTER [GLYCINE,N [AT 13-HYDROXY 1 -[ (PHENYLMETH-OXY)CARBONYL] -L PROLYL] GLYCYL] -, ETHYL ESTER], 88 Propane, 1-mtro-, 36 1,3 Propanedithiol, 9 Propanoic acid, 2-chloro-, 70 1-PROPENE, 3 ACETOXY-2-BROMO-1,1-D1PHENYL- [2-PROPFN-l-OI, 2-BROMO 3,3 DIPHENYL, ... 

Allene, l,3-di-ferf-butyl-l,3-dicyano- [2,3-Pentadienedimtnle, 2,4-bis(l,l-di-methylethyl) ], 55, 38 ALLYL ALCOHOL [2 Propen 1 ol], 55, 1 Amberhte IRA-400, 55, 5 Amine, diethyl- [Ethanamme, IV-ethyl-],... 

PROPENOIC ACID, 3-NITRO-, ETHYL ESTER, (E)- [5941-50-4], 56,65 2-PROPEN-l-OL, 55,1 2-BROMO-3,3-DIPHENYL-, ACETATE [14310-15-71,56, 32... 

It was thought that propionitrile came from dehydrogenation of the anti-Markovnikov hydroamination product, w-PrNHj. Propionitrile can break down to ethylene and HCN, the former reacting with NH3 to generate acetonitrile via ethyl-amine, the latter adding to propene to form the butyronitriles [26, 37]. 

Cyclohexane Methylcyclohexane Phenol Terpenes Turpentine Alcohols Methyl alcohol Ethyl alcohol 2-propen-l-ol n-Propyl alcohol Isopropyl alcohol n-Butyl alcohol Amyl alcohol Isoamyl alcohol Aldehydes Formaldehyde Acetaldehyde Acrolein... 

The results of the olefin oxidation catalyzed by 19, 57, and 59-62 are summarized in Tables VI-VIII. Table VI shows that linear terminal olefins are selectively oxidized to 2-ketones, whereas cyclic olefins (cyclohexene and norbomene) are selectively oxidized to epoxides. Cyclopentene shows exceptional behavior, it is oxidized exclusively to cyclopentanone without any production of epoxypentane. This exception would be brought about by the more restrained and planar pen-tene ring, compared with other larger cyclic nonplanar olefins in Table VI, but the exact reason is not yet known. Linear inner olefin, 2-octene, is oxidized to both 2- and 3-octanones. 2-Methyl-2-butene is oxidized to 3-methyl-2-butanone, while ethyl vinyl ether is oxidized to acetaldehyde and ethyl alcohol. These products were identified by NMR, but could not be quantitatively determined because of the existence of overlapping small peaks in the GC chart. The last reaction corresponds to oxidative hydrolysis of ethyl vinyl ether. Those olefins having bulky (a-methylstyrene, j8-methylstyrene, and allylbenzene) or electon-withdrawing substituents (1-bromo-l-propene, 1-chloro-l-pro-pene, fumalonitrile, acrylonitrile, and methylacrylate) are not oxidized. 

---