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

Year 2017, Volume: 6 Issue: 2, 7 - 10, 16.12.2017

Abstract



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).




References

  • [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.

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

Year 2017, Volume: 6 Issue: 2, 7 - 10, 16.12.2017

Abstract



Bu çalışmada,
bisiklik halka sistemine sahip bileşiklerden elektrokimyasal indirgenme ile
alken sentezi yapıldı. Gerekli başlangıç bileşikleri, endoperoksit ve trans-7,8-dibromo-cis-2,5-dihidroksibisiklo [4.2.0] okta-3-en sentetik yöntemler
kullanılarak hazırlandı.
Bu
bileşiklere elektrokimyasal indirgenme yöntemi uygulanarak cis-2,5-diasetoksi-bisiklo [4.2.0] okta-3,7-dien ve bisiklo [4.2.0]
okta-3,7-dien elde edildi. Elde edilen tüm bileşiklerin yapıları spektroskopik
teknikler (FT-IR, 1H- 13C-NMR) kullanılarak belirlendi.




References

  • [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.
There are 27 citations in total.

Details

Subjects Engineering
Journal Section Articles
Authors

Latif Kelebekli

Yunus Kara This is me

Publication Date December 16, 2017
Published in Issue Year 2017 Volume: 6 Issue: 2

Cite

APA Kelebekli, L., & Kara, Y. (2017). Elektrokimyasal yöntemle Visinal trans-1,2-Dibromür bileşiklerinden Alken sentezi. Türk Doğa Ve Fen Dergisi, 6(2), 7-10.
AMA Kelebekli L, Kara Y. Elektrokimyasal yöntemle Visinal trans-1,2-Dibromür bileşiklerinden Alken sentezi. TJNS. December 2017;6(2):7-10.
Chicago Kelebekli, Latif, and Yunus Kara. “Elektrokimyasal yöntemle Visinal Trans-1,2-Dibromür bileşiklerinden Alken Sentezi”. Türk Doğa Ve Fen Dergisi 6, no. 2 (December 2017): 7-10.
EndNote Kelebekli L, Kara Y (December 1, 2017) Elektrokimyasal yöntemle Visinal trans-1,2-Dibromür bileşiklerinden Alken sentezi. Türk Doğa ve Fen Dergisi 6 2 7–10.
IEEE L. Kelebekli and Y. Kara, “Elektrokimyasal yöntemle Visinal trans-1,2-Dibromür bileşiklerinden Alken sentezi”, TJNS, vol. 6, no. 2, pp. 7–10, 2017.
ISNAD Kelebekli, Latif - Kara, Yunus. “Elektrokimyasal yöntemle Visinal Trans-1,2-Dibromür bileşiklerinden Alken Sentezi”. Türk Doğa ve Fen Dergisi 6/2 (December 2017), 7-10.
JAMA Kelebekli L, Kara Y. Elektrokimyasal yöntemle Visinal trans-1,2-Dibromür bileşiklerinden Alken sentezi. TJNS. 2017;6:7–10.
MLA Kelebekli, Latif and Yunus Kara. “Elektrokimyasal yöntemle Visinal Trans-1,2-Dibromür bileşiklerinden Alken Sentezi”. Türk Doğa Ve Fen Dergisi, vol. 6, no. 2, 2017, pp. 7-10.
Vancouver Kelebekli L, Kara Y. Elektrokimyasal yöntemle Visinal trans-1,2-Dibromür bileşiklerinden Alken sentezi. TJNS. 2017;6(2):7-10.

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