@article{KruegerBramborgKellingetal.2021,
  author    = {Kr{\"u}ger, Tobias and Bramborg, Andrea and Kelling, Alexandra and Sperlich, Eric and Linker, Torsten},
  title     = {Birch Reduction of Arenes as an Easy Entry to γ-Spirolactones},
  series = {European journal of organic chemistry},
  volume    = {2021},
  journal   = {European journal of organic chemistry},
  number    = {46},
  publisher = {Wiley-VCH},
  address   = {Weinheim},
  issn      = {1434-193X},
  doi       = {10.1002/ejoc.202101018},
  pages     = {6383 -- 6391},
  year      = {2021},
  abstract  = {A convenient method for the synthesis of γ-spirolactones in only 2-3 steps is described. Birch reduction of inexpensive and commercially available aromatic carboxylic acids in the presence of ethylene oxide affords hydroxy acids, which undergo direct lactonization during work-up. Suitable precursors are methyl-substituted benzoic acids, naphthoic, and dicarboxylic acids. Subsequent hydrogenation proceeds smoothly with Pd/C as catalyst and saturated γ-spirolactones are isolated in excellent yields and stereoselectivities. Thus, up to 3 new stereogenic centers can be constructed as sole diastereomers from achiral benzoic acids. Furthermore, it is possible to control the degree of saturation with Raney nickel or Wilkinson's catalyst to obtain products with 1 double bond. Overall, more than 30 new γ-spirolactones have been synthesized in analytically pure form.},
  language  = {en}
}
@article{BramborgLinker2012,
  author    = {Bramborg, Andrea and Linker, Torsten},
  title     = {Regioselective synthesis of alkylarenes by two-step ipso-substitution of aromatic dicarboxylic acids},
  series = {European journal of organic chemistry},
  journal   = {European journal of organic chemistry},
  number    = {28},
  publisher = {Wiley-VCH},
  address   = {Weinheim},
  issn      = {1434-193X},
  doi       = {10.1002/ejoc.201200823},
  pages     = {5552 -- 5563},
  year      = {2012},
  abstract  = {A strategy for the regioselective alkylation of arenes was developed, starting from commercially available and inexpensive terephthalic acid or naphthalene-1,4-dicarboxylic acid. The method entails a formal ipso-substitution of the carboxylate groups by a sequence of reductive alkylation under Birch conditions and subsequent acid-mediated rearomatization with loss of carbon monoxide and carbon dioxide. More than 20 different arenes with various side-chains were synthesized. With naphthalene-1,4-dicarboxylic acid as starting material, we were able to control the degree of alkylation by choosing the appropriate electrophile in the Birch reduction. Thus, bisalkylated naphthalenes and naphthoic acids became available chemoselectively. All reactions afforded a single regioisomer exclusively in high yields. Overall, aromatic dicarboxylic acids are suitable substrates for a two-step ipso-substitution that allows the selective synthesis of alkylated benzenes and naphthalenes.},
  language  = {en}
}
@article{LinkerBramborgKellingetal.2013,
  author    = {Linker, Torsten and Bramborg, Andrea and Kelling, Alexandra and Schilde, Uwe},
  title     = {Crystal structure of trans-1,4-di-(2-(allyloxyethyl)-cyclohexa-2,5-diene-1,4-dicarboxylic acid, C18H24O6},
  series = {Zeitschrift f{\"u}r Kristallographie : international journal for structural, physical and chemical aspects of crystalline materials ; New crystal structures},
  volume    = {228},
  journal   = {Zeitschrift f{\"u}r Kristallographie : international journal for structural, physical and chemical aspects of crystalline materials ; New crystal structures},
  number    = {2},
  publisher = {De Gruyter Oldenbourg},
  address   = {M{\"u}nchen},
  issn      = {1433-7266},
  doi       = {10.1524/ncrs.2013.0124},
  pages     = {243 -- 244},
  year      = {2013},
  abstract  = {C18H24O6, triclinic, P (1) over bar (no. 2), a = 5.726(1) angstrom, b = 8.845(2) angstrom, c = 9.557(2) angstrom, alpha = 105.27(1)degrees, beta = 102.76(1)degrees, gamma = 103.49(1)degrees, V = 433.0 angstrom(3), Z = 1, R-gt(F) = 0.0412, wR(ref)(F-2) = 0.1075, T = 210 K.},
  language  = {en}
}
@phdthesis{Bramborg2011,
  author    = {Bramborg, Andrea},
  title     = {Regioselektive Synthese von Alkylarenen durch ipso-substitution aromatischer Carbons{\"a}uren},
  address   = {Potsdam},
  pages     = {163 S.},
  year      = {2011},
  language  = {de}
}
@article{BramborgLinker2010,
  author    = {Bramborg, Andrea and Linker, Torsten},
  title     = {Selective synthesis of 1,4-dialkylbenzenes from terephthalic acid},
  issn      = {1615-4150},
  doi       = {10.1002/adsc.201000322},
  year      = {2010},
  abstract  = {Terephthalic acid reacts with alkyl halides under Birch conditions to substituted 1,4-cyclohexadienes in high yields and good stereoselectivities. Electrophiles containing ester or nitrile groups undergo a surprising fragmentation under the reaction conditions. Subsequent treatment with chlorosulfonic acid proceeds by an interesting tandem decarbonylation/decarboxylation, affording 1,4-dialkylbenzenes in excellent regioselectivity. Thus our new method is superior to classical Friedel-Crafts alkylations.},
  language  = {en}
}