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Breit, Bernhard; Regitz, Manfred

Organophosphorus Compounds, 112. Lewis Acid Mediated Spirocyclotrimerization of Kinetically Stabilized Phosphaalkynes – Key Step for the Selective Generation and Trapping of Triphospha Dewar Benzenes

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  • Medientyp: E-Artikel
  • Titel: Organophosphorus Compounds, 112. Lewis Acid Mediated Spirocyclotrimerization of Kinetically Stabilized Phosphaalkynes – Key Step for the Selective Generation and Trapping of Triphospha Dewar Benzenes
  • Beteiligte: Breit, Bernhard; Regitz, Manfred
  • Erschienen: Wiley, 1996
  • Erschienen in: Chemische Berichte
  • Sprache: Englisch
  • DOI: 10.1002/cber.19961290504
  • ISSN: 0009-2940
  • Schlagwörter: Inorganic Chemistry
  • Entstehung:
  • Anmerkungen:
  • Beschreibung: <jats:title>Abstract</jats:title><jats:p>In the presence of Lewis acidic derivatives of group 13 elements, phosphaalkynes <jats:bold>7</jats:bold> undergo spirocyclotrimerization with incorporation of the corresponding Lewis acids to form <jats:bold>10a–f</jats:bold>. Scope and limitations of this novel cyclooligomerization process are examined. Starting from the spirocyclotrimer <jats:bold>10a</jats:bold> reaction with the Lewis base dimethyl sulfoxide, we have in hand for the first time a method for the selective generation of two isomeric triphospha Dewar benzene derivatives (<jats:bold>18, 19</jats:bold>). Both can be trapped efficiently by further reaction with the phosphaalkyne to furnish the two novel phosphaalkyne cyclotetramers <jats:bold>20</jats:bold> and <jats:bold>21</jats:bold>, both still possessing a phosphorus–carbon double bond. In the case of <jats:bold>21</jats:bold>, further functionalization of the phosphaalkene unit is possible by [3 + 2] cycloaddition with a nitrile oxide (→ <jats:bold>23</jats:bold>).</jats:p>