Reactivities of Stable Rotamers. XXXV. Diazotization of 2-(1,4-Dimethyl-9-triptycyl)-2-methyl-Propylamine Rotamers

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Author(s)

    • OKI Michinori
    • Department of Chemistry, Faculty of Science, Okayama University of Science
    • TAGUCHI Yasushi
    • Department of Chemistry, Faculty of Science, Okayama University of Science
    • MIYASAKA Tsutomu
    • Department of Chemistry, Faculty of Science, Okayama University of Science
    • KITNO Mika
    • Department of Chemistry, Faculty of Science, Okayama University of Science
    • TOYOTA Shinji
    • Department of Chemistry, Faculty of Science, Okayama University of Science
    • YAMAMOTO Gaku
    • Department of Chemistry, Faculty of Science, The University of Tokyo

Abstract

The title amine rotamers were prepared from the corresponding carboxylic acids and were diazotized with isopentyl nitrite in the presence of acetic acid in benzene. The <i>ap</i> rotamer affords, as main products, olefins that are derived by deprotonation after rearrangement of the intervening carbocation and small amounts each of the corresponding acetate and a cyclized product, both of which are derived from the unrearranged cation. By contrast, the olefins are minor products and a cyclized product, which is formally derived by insertion of the intervening cation to a C–H bond of the 1-methyl group before rearrangement, is main in the case of the <i>sc</i> isomer. This cyclic product was synthesized independently. The yield of the corresponding acetate is increased to a considerable extent in the case of the <i>sc</i> relative to the <i>ap</i>. These results in the reaction of the <i>sc</i> are discussed in terms of stabilization of the intervening cation by the C–H bond.

Journal

  • Bulletin of the Chemical Society of Japan

    Bulletin of the Chemical Society of Japan 68(5), 1485-1496, 1995-05-15

    The Chemical Society of Japan

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Codes

  • NII Article ID (NAID)
    10008890051
  • NII NACSIS-CAT ID (NCID)
    AA00580132
  • Text Lang
    ENG
  • Article Type
    ART
  • ISSN
    00092673
  • Data Source
    CJP  J-STAGE 
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