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The synthesis and characterization of N-tosyl halodihydroconduramines from corresponding mono-epoxy derivative

Kurbanoglu, Namudar Izzet; Baran, Arif; Col, Sumeyye


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        "affiliation": "Sakarya Univ, Fac Educ, Dept Sci Educ, TR-54300 Hendek Sakarya, Turkey", 
        "name": "Kurbanoglu, Namudar Izzet"
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      {
        "affiliation": "Sakarya Univ, Dept Chem, Fac Art & Sci, TR-54100 Esentepe Sakarya, Turkey", 
        "name": "Baran, Arif"
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      {
        "affiliation": "Sakarya Univ, Dept Chem, Fac Art & Sci, TR-54100 Esentepe Sakarya, Turkey", 
        "name": "Col, Sumeyye"
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    "description": "Cyclitols and their halogen derivatives are important compounds in organic chemistry, and thus their synthesis with high efficiency has gained importance. In this study, BX3-assisted (X=Br or Cl) ring-opening reactions of the mono-epoxide 15 of [(3aR(S),7aS(R))]-2,2-dimethyl-3-tosyl-2,3,3a,6,7,7a-hexahydrobenzo[d]oxazole (12) have been investigated. In BX3-assisted (BBr3 or BCl3) ring-opening processes, this epoxide reacts exclusively via nucleophilic attack at carbon 3a-C of the substrate and such regioselectivity has been exploited in the synthesis of the N-tosyl bromo- and N-tosyl chloro-dihydroconduramines. The structures of the products were established by chemical correlation studies.", 
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      "pages": "105-113", 
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