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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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{
  "DOI": "10.24820/ark.5550190.p011.090", 
  "abstract": "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.", 
  "author": [
    {
      "family": "Kurbanoglu", 
      "given": " Namudar Izzet"
    }, 
    {
      "family": "Baran", 
      "given": " Arif"
    }, 
    {
      "family": "Col", 
      "given": " Sumeyye"
    }
  ], 
  "container_title": "ARKIVOC", 
  "id": "4971", 
  "issued": {
    "date-parts": [
      [
        2020, 
        1, 
        1
      ]
    ]
  }, 
  "page": "105-113", 
  "title": "The synthesis and characterization of N-tosyl halodihydroconduramines from corresponding mono-epoxy derivative", 
  "type": "article-journal"
}
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