Elektrokimyasal yöntemle Visinal trans-1,2-Dibromür bileşiklerinden Alken sentezi

Latif Kelebekli; Yunus Kara

Araştırma Makalesi

Synthesis of Alkenes from Vicinal trans-1,2-Dibromide compounds by electrochemical methods

Yıl 2017, Cilt: 6 Sayı: 2, 7 - 10, 16.12.2017

Latif Kelebekli , Yunus Kara

Öz

In this work, alkene
synthesis was carried out by electrochemical reduction of compounds having a
bicyclic ring system. The required starting compounds were prepared the
endoperoxide and trans-7,8-dibromo-cis-2,5-dihydroxybicyclo [4.2.0]
octa-3-ene using synthetic methods. Electrochemical reduction method was
applied to these compounds and obtained the cis-2,5-diacetoxy-bicyclo
[4.2.0] octa-3,7-diene and bicyclo [4.2.0] octa-3,7-diene. The structures of
all compounds obtained were determined using spectroscopic techniques (FT-IR, ¹H-¹³C-NMR).

Anahtar Kelimeler

Electrochemical reduction, cathodic reduction

Kaynakça

[1] Vollhardt K.P.C., Schore N.E., Organic chemistry, structure and function, 3th, p 493-496, 1998, USA.
[2] Dillon R.T., The reaction rate of potassium iodide with dibromides of the ethylene bromide type, J. Am. Chem. Soc., 54, 952-960, 1932.
[3] Goering H.L., Espy H.H., The iodide ion-promoted dehalogenation of cis- and trans-1,2-dihalocyclohexanes, J. Am. Chem. Soc., 77, 5023-5026, 1955.
[4] Mathai I.M., Schug K., Miller S.I., Stereoselectivity in the debromination of the stilbene dibromides by several metals and inorganic reductants in several solvents, J. Org. Chem., 35, 1733-1736, 1970.
[5] Adam W., Arce J., Stereospecific dehalogenation of vic-dibromides by sodium naphthalenide, J. Org. Chem., 37, 507-508, 1972.
[6] Schubert M., Rabinovitch, B.S., Larson N.R., Sims V.A., The stereochemistry of the debromination of vicinal dibromides by metals, J. Am. Chem. Soc., 74 (18), 4590-4592, 1952.
[7] Buckles R.E., Bader J.M., Thurmaier R.J., Stereospecificity of the addition of bromine to cis- and trans-stilbene, J. Org. Chem., 27, 4523-4527, 1962.
[8] Prince M., Bremer B.W., Brenner W., Sodium selenide vicinal dihalide elimination, J. Org. Chem., 31 (12), 4292-4293, 1966.
[9] Vijayashree N., Samuelson A.G., Selective debromination of activated vicinal dibromides by copper promoted by copper (II), Tetrahedron Lett., 33, 559-560, 1992.
[10] Fukunage K.,Yamaguchi H., Debromination of vic-dibromides with sodium sulfide in dimethylformaide, Synthesis 879-880, 1981.
[11] Olah G.A., Prakash G.K.S., Synthetic methods and reactions; XVIII. Preparation of alkenes via dehalogenation of vic-dihaloalkanes, coupling of allyl and benzyl halides, dehalogenative coupling of aryl-gem-dihaloalkanes using TiCl3- or TiCl4/LiAlH4 reagent, Synthesis 9, 607-609, 1976.
[12] Halpern J., Maher J.P., Kinetics of the reactions of pentacyanocobaltate (II) with organic halides, J. Am. Chem. Soc., 87, 5361-5366, 1965.
[13] Butcher T.S., Zhou F., Detty M.R., Debrominations of vic-dibromides with diorganotellurides.1. Stereoselectivity, relative rates, and mechanistic implications, J. Org. Chem. 63, 169-176, 1998.
[14] Wang L., Zhang Y., Metallic samarium promoted reductive dimerization cyclization of gem-diactivated alkenes, reductive debromination of vic-dibromides, and reduction of sodium alkyl thiosulfates in aqueous media, Tetrahedron 55, 10695-10712, 1999.
[15] Ranu B.C., Guchhait S.K., Sarkar A., Stereoselective debromination of aryl-substituted vic-dibromide with indium metal, Chem. Commun., 2113-2114, 1998.
[16] Malanga C., Mannucci S., Lardicci L., Carbon-halogen bond activation by nickel catalyst: Synthesis of alkenes, from 1,2-dihalides, Tetrahedron 54,1021-1028, 1998.
[17] Sarma J.C., Borbaruah M., Sharma R.P., Dehalogenation of α-haloketons and vic-dibromides with nickel boride, Tetrahedron Lett., 26, 4657-4660, 1985.
[18] Andrieux C.P., Le Gorande A., Saveant J.M., Reductive elimination in vicinal dibromides. Electrochemical reduction of 1,2-dibromo-3-(4-substituted)-phenylpropanes and induction of double-bond migration in the resulting olefins. J. Electroanal. Chem., 371, 191-196, 1994.
[19] Bowyer W.J., Evans D.H., Electron transfer reactions and associated conformational changes. Electrochemical reduction of trans-1,2- diiodocyclohexane, J. Electroanal. Chem., 240, 227-237, 1998.
[20] Inesi A., Rampazzo L., Stereoselective reduction of meso- and dl-1,2-dibromo-1,2-diphenylethane at the mercury electrode, Electroanal. Chem. Interf. Electrochem., 54, 289-995, 1974.
[21] Kelebekli L., Demir Ü., Kara Y., Direct synthesis of trans-1,4-diacetoxycyclohexa-2,5-diene by electrochemical reduction of r-1,t-4-diacetoxyt-2,c-3-dibromocyclohex-5-ene, J. Chem. Research (S), 402–403, 1997.
[22] Huisgen R., Boche G., Zum mechanismus der bromierung des cyclooctatetraens, Tetrahedron Lett., 23, 1769-771, 1965.
[23] Fray G.I., Saxton R.G., The chemistry of cyclooctatetraen and its derivatives, Cambridge University press, Cambridge, p 18, 1978.
[24] Oda M., Kayama Y., Kitahara Y., Synthesis of bicyclo[4.2.0]octa 3,7-diene-2,5-dione, Tetrahedron Lett., 23, 2019-2022, 1974.
[25] Kelebekli L., Kara Y., Balci M., Stereospecific synthesis of a new class of compounds: bis-homoconduritol-A, -D, and -F, Carbohydr. Res., 340, 1940-1948, 2005.
[26] O'Connell K.M., Evans D.H., Electron-transfer reactions and associated conformational changes. Electrochemical reduction of some vicinal dibromides, J. Am. Chem. Soc. 105, 1473-1481,1983.
[27] Casanova J., Rogers H.R., Electroorganic chemistry. II. Electroreduction of vicinal dibromides, J. Org. Chem., 39, 2408-2410, 1974.