Pent-2-ene

JA173) illustrates this possibility (Scheme 34). Thus 3,3,5-trimethyl-3//-pyrazole (371 R = H) on irradiation in pentane solution gives 1,3,3-trimethylcyclopropene (372 R = H) the intermediate diazoalkene (373) has been characterized. The tetramethyl derivative (371 R" = Me) when irradiated at -50 °C in methylene chloride leads to a species believed to be a l,2-dlazablcyclo[2.1.0]pent-2-ene (374). This isomerization is thermally reversible, the 3H- pyrazole being regenerated at room temperature. 

UV spectra, S, 844 Pent-2-ene, perfluoro-2-methyl-2H-pyran synthesis from, 3, 740 Pent-2-enedioic acid, 2,4-diacetyl-esters... 

The synthetic utility of the alkene metathesis reaction may in some cases be limited because of the formation of a mixture of products. The steps of the catalytic cycle are equilibrium processes, with the yields being determined by the thermodynamic equilibrium. The metathesis process generally tends to give complex mixtures of products. For example, pent-2-ene 8 disproportionates to give, at equilibrium, a statistical mixture of but-2-enes, pent-2-enes and hex-3-enes ... 

Most cyclic and acyclic 1,3-dienes, such as cyclopentadiene, undergo photochemical ring-closure to cyclobutenes. Cyclopentadiene-<5-d, cyclopentadiene-d, 2-methyleyclopentadiene,1 and 1-methylcyclo-pentadiene11 have been converted to the corresponding bicyelo-[2.1.0]pent-2-ene derivatives. 

The recent upsurge of interest in systems of theoretical interest demands practical syntheses of several important compounds. These are BICYCLO[2.l.0]PENT-2-ENE, BENZOCYCLOPROPENE, 1,6-OXIDO[10]ANNULENE, and others. ewdo-TRICYCLO[4.4.0.02 5]-DECA-3,8-DIENE-7,10-DIONE is utilized as a model for the use of CYCLOBUTADIENE IN SYNTHESIS, and a stable monomeric ketene, icri-BUTYLCYANOKETENE offers opportunities for further studies of this interesting species. 

The stereospeciflcity of dehalogenation of vicinal dibromides to olefins was examined for reducing agents including Cr(II), iodide, and Fe° (Totten et al. 2001). For dibromostilbene, the ( )-stilbene represented >70% of the total olefin that was produced, and for threo-dibromopentane reduction by Cr(Il) produced ca. 70% of ( )-pent-2-ene, whereas values for iodide and Fe° were <5% of this. 

FIGURE 7.15 Biodegradability of enantiomeric of epoxides of cis- and fraws-pent-2-enes. 

C2O-C3O l,4-Dioxa-spiro[2.3]hexane 2, 371 5-Thia-bicyclo[2.1.0]pent-2-ene 1, 398... 

Scheme 1. Tungsten catalysed cross-metathesis of allyl methyl sulphide with pent-2-ene and but-2-ene...

The successful cross-metathesis of allyl methyl sulphide with ris-pent-2-ene and czs-but-2-ene, catalysed by the tungsten alkylidene 5, was reported by Basset and co-workers in 1993 [20] (Scheme 1). 

Using an equimolar quantity of allyl methyl sulphide and ds-pent-2-ene resulted in incomplete reaction of the allyl sulphide and some self-metathesis of the sulphide substrate. When an excess (4 equiv) of but-2-ene was used, however, the desired but-2-enyl sulphide was formed in a good yield at ambient temperature. In this case, the large quantities of unwanted hydrocarbon starting material and self-metathesis products were gaseous alkenes and therefore easily removed. Using a large excess of one alkene to improve the yield of the desired cross-metathesis product in this way is obviously only viable if this alkene is inexpensive and both it and its self-metathesis product are easily removed. 

When quinalbarbitone (secobarbital, 296) was irradiated in acid solution (pH 2) at 254 nm, it underwent photodealkylation to give (297), (298), pent-l-ene and pent-2-ene. These four compounds were also obtained at pH 10, but in addition there were the ring-opened materials (299) to (301), Scheme 2.7 [ 176],... 

Azatricyclo[2.2.1.02 6]hept-7-yl perchlorate, 2368 f Azetidine, 1255 Benzvalene, 2289 Bicyclo[2.1.0]pent-2-ene, 1856 2-/ert-Butyl-3-phenyloxaziridine, 3406 3 -Chloro-1,3 -diphenyleyclopropene, 3679 l-Chloro-2,3-di(2-thienyl)cyclopropenium perchlorate, 3388 Cyanocyclopropane, 1463 f Cyclopropane, 1197 f Cyclopropyl methyl ether, 1608 2,3 5,6-Dibenzobicyclo[3.3.0]hexane, 3633 3,5 -Dibromo-7-bromomethy lene-7,7a-dihy dro-1,1 -dimethyl-1H-azirino[l,2-a]indole, 3474 2.2 -Di-tert-butyl-3.3 -bioxaziridinc, 3359 Dicyclopropyldiazomethane, 2824 l,4-Dihydrodicyclopropa[ >, g]naphthalene, 3452 iV-Dimethylethyl-3,3-dinitroazetidine, 2848 Dinitrogen pentaoxide, Strained ring heterocycles, 4748 f 1,2-Epoxybutane, 1609 f Ethyl cyclopropanecarboxylate, 2437 2,2 -(l,2-Ethylenebis)3-phenyloxaziridine, 3707 f Methylcyclopropane, 1581 f Methyl cyclopropanecarboxylate, 1917 f Oxetane, 1222... 

Synonyms p /3-Amylene cis-P-Amylene EINECS 203-695-0 EINECS 210-988-7 EINECS 261-403-7 EINECS 273-308-8 c/s-Methylethyl ethylene NSC 7894 c/5-Pentene-2 c/5-Pent-2-ene ( -2-Pentene UN 1993. 

The elimination of hydrogen halides from some monohaloalkanes can result in the formation of two alkenes. Consider 2-bromopentane, for example. You can see from its structure that the elimination of HBr will produce both pent-l-ene and pent-2-ene. 

If there is possibility of formation of more than one alkene due to the availability of more than one 3-hydrogen atoms, usually one alkene is formed as the major produet. These form part of a pattern first observed by Russian ehemlst, Alexander Zaitsev (also pronounced as Saytzeff) who In 1875 formulated a rule which can be summarised as in dehydrohalogenation reactions, the preferred product is that alkene which has the greater number of alkyl groups attached to the doubly bonded carbon atoms. Thus, 2-bromopentane gives pent-2-ene as the major product. 

Intriguingly, although there are going to be two different and enantiomeric bromonium ions for an unsymmetrical substrate such as (Z)-pent-2-ene, a... 

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