Abstract
Naphthalene and alkylnaphthalenes are electro-oxidized to give many products, of which 1,4-naphthoquinones and binaphthyls are the most stable, especially in the case of substrates, which are not substituted in α-positions. On the other hand, α-substituted naphthalenes give the respective naphthoquinols as the main products. Interestingly, 1,2-naphthoquinones are not separated as products, instead, a fragmentation of one of the rings leads to oxidation products, in which the 1,2-bond in naphthalene is broken to form dialdehydes or diketones. An anodic formation of binaphthyls is described, starting from alkyl-substituted naphthalenes, dissolved in acetone-water (1:1 v/v) and using 0.1 M (CH3)4N(BF4) supporting electrolyte. Several isomeric binaphthyls were obtained depending on the substrates. The structure of the binaphthyls formed is discussed based on molecular orbital calculations using the AM1 program. Cyclic voltammetric oxidation curves are shown for naphthalene and three methyl derivatives.
References
GJ Hoijtink WP Weijland (1957) Rec Trav Chim 76 836 Occurrence Handle1:CAS:528:DyaG1cXisVWgtg%3D%3D Occurrence Handle10.1002/recl.19570761012
GJ Hoijtink (1958) Rec Trav Chim 77 555 Occurrence Handle1:CAS:528:DyaG1cXhtFWhsL8%3D Occurrence Handle10.1002/recl.19580770605
M Schmittel A Burghart (1997) Angew Chem Int Ed Engl 36 2551 Occurrence Handle1:CAS:528:DyaK1cXjtVGntQ%3D%3D
RE Sioda (1968) J Phys Chem 72 2322 Occurrence Handle10.1021/j100853a007 Occurrence Handle1:CAS:528:DyaF1cXksVylu74%3D
Y Mao A Bakac (1997) J Phys Chem A 101 7929 Occurrence Handle10.1021/jp962961z Occurrence Handle1:CAS:528:DyaK2sXmsVehtro%3D
Y Kuroda A Kunai M Hamada T Kitano S Ito K Sasaki (1991) Bull Chem Soc Jpn 64 3089 Occurrence Handle10.1246/bcsj.64.3089 Occurrence Handle1:CAS:528:DyaK38XlvVGiug%3D%3D
NJ Bunce L Liu J Zhu (1997) Environ Sci Technol 31 2252 Occurrence Handle10.1021/es960813g Occurrence Handle1:CAS:528:DyaK2sXjvFCgsbc%3D
J Sasaki SM Aschmann ESC Kwok R Atkinson J Arey (1997) Environ Sci Technol 31 3173 Occurrence Handle10.1021/es9701523 Occurrence Handle1:CAS:528:DyaK2sXmt1emt7o%3D
JRL Smith BAJ Shaw DM Foulkes AM Jeffrey DM Jerina (1977) J Chem Soc Perkin Trans 2 1583
F Soanna M Sturini L Cermenati A Albini (2000) J Chem Soc Perkin Trans 2 699
RA Larson WJ Garrison KA Marley (1986) Tetrahedron Lett 27 3987 Occurrence Handle10.1016/S0040-4039(00)84891-1 Occurrence Handle1:CAS:528:DyaL2sXkt1ejtr4%3D
Boyland E, Sims P (1953) J Chem Soc:2966
M Panizza G Cerisola (2003) Electrochim Acta 48 3491 Occurrence Handle10.1016/S0013-4686(03)00468-7 Occurrence Handle1:CAS:528:DC%2BD3sXmvF2hu78%3D
M Panizza G Cerisola (2004) Electrochim Acta 49 3221 Occurrence Handle10.1016/j.electacta.2004.02.036 Occurrence Handle1:CAS:528:DC%2BD2cXjvFKks7k%3D
LK Sydnes IC Burkov SH Hansen (1985) Tetrahedron 41 5706
RE Sioda B Frankowska (2004) J Electroanal Chem 568 365 Occurrence Handle10.1016/j.jelechem.2004.01.030 Occurrence Handle1:CAS:528:DC%2BD2cXktFKqtLg%3D
GA Bhat M Periasamy MV Bhatt (1979) Tetrahedron Lett 33 3097 Occurrence Handle10.1016/S0040-4039(01)95329-8
H Greenland JT Pinhey S Sternhell (1987) Aust J Chem 40 325 Occurrence Handle1:CAS:528:DyaL2sXlslGlsLk%3D Occurrence Handle10.1071/CH9870325
J Carnduff M Hafiz R Hendrie F Monaghan (1984) Tetrahedron Lett 25 6033 Occurrence Handle10.1016/S0040-4039(01)81753-6 Occurrence Handle1:CAS:528:DyaL2MXhvVCqs7s%3D
GA Bhat M Periasamy MV Bhatt (1979) Tetrahedron Lett 33 3097 Occurrence Handle10.1016/S0040-4039(01)95329-8
M Tanaka H Nakashima M Fujiwara H Ando Y Souma (1996) J Org Chem 61 788 Occurrence Handle10.1021/jo950814b Occurrence Handle1:CAS:528:DyaK28Xis1Oiuw%3D%3D
M Tanaka E Muro H Ando Q Xu M Fujiwara Y Souma Y Yamaguchi (2000) J Org Chem 65 2972 Occurrence Handle10.1021/jo991538u Occurrence Handle1:CAS:528:DC%2BD3cXis1Oqu7g%3D
W Jaworek F Voegtle (1991) Chem Ber 124 347 Occurrence Handle10.1002/cber.19911240216 Occurrence Handle1:CAS:528:DyaK3MXhtVWgs7c%3D
L Eberson MP Hartshorn O Persson (1995) J Chem Soc Perkin Trans 2 409
Eberson L, Hartshorn MP, Persson O, Robinson WT, Timmerman-Vaughan DJ (1995) Acta Chem Scand:49
J March (1992) Advanced Organic Chemistry EditionNumber4 John Wiley New York 539
Millauer H (1995) Ger Pat DE 4342282
JHP Utley GG Rozenberg (2002) Tetrahedron 58 5251 Occurrence Handle10.1016/S0040-4020(02)00495-7 Occurrence Handle1:CAS:528:DC%2BD38XkvVWktL8%3D
JJP Stewart (1998) WinMOPAC 2.0, User Manual Fujitsu Limited Tokyo, Japan
MR Spiegel (1968) Mathematical Handbook McGraw-Hill New York 47
TL Gilchrist RC Storr (1972) Organic reactions and orbital symmetry Cambidge University Press Cambridge
RE Sioda B Frankowska A Łobuzińska TZ Fahidy (2004) Pol J Chem 78 1567 Occurrence Handle1:CAS:528:DC%2BD2cXhtVWisbbF
E Zadok S Rubinraut Y Mazur (1984) Tetrahedron Lett 25 4175 Occurrence Handle10.1016/S0040-4039(01)90214-X Occurrence Handle1:CAS:528:DyaL2cXmtlSjtLo%3D
D Kuck (1994) Org Mass Spectrom 29 113 Occurrence Handle10.1002/oms.1210290302 Occurrence Handle1:CAS:528:DyaK2cXktlClsb0%3D
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Correspondence: Roman Edmund Sioda, Department of Analytical Chemistry and Electrochemistry, Institute of Chemistry of University of Podlasie, ul. 3 Maja 54, 08-110 Siedlce, Poland.
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Sioda, R., Frankowska, B. & Lesiak, E. Electro-oxidation of certain naphthalene derivatives. Monatsh Chem 139, 513–519 (2008). https://doi.org/10.1007/s00706-007-0818-8
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DOI: https://doi.org/10.1007/s00706-007-0818-8