On the road to stable, isolable [4]cumulenes: Reactivity and cyclization reactions

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<jats:title>Abstract</jats:title><jats:p>The design and synthesis of persistent tetraaryl[4]cumulenes are reported. Derivatives with phenyl endgroups (<jats:bold>[4]Ph</jats:bold> and <jats:bold>[4]Ph/Ar*</jats:bold>) are susceptible to reactions during synthesis and/or purification that complicate isolation of the desired product, particularly intermolecular dimerization reactions. Incorporation of (3,5‐di‐<jats:italic>tert</jats:italic>‐butyl)phenyl endgroups (Ar*) provides increased stability, culminating in the stable and isolable [4]cumulene <jats:bold>[4]Ar*</jats:bold>. Cumulene <jats:bold>[4]Ar*</jats:bold> remains, however, susceptible to dimerization under pressing conditions, and <jats:bold>[4]Ar*</jats:bold> also readily reacts with electrophiles under mild conditions that lead to intramolecular cyclization. Given the structural complexity of the side products in these studies (compounds <jats:bold>3</jats:bold>, <jats:bold>10</jats:bold>, <jats:bold>14</jats:bold>, <jats:bold>17</jats:bold>, <jats:bold>18</jats:bold>), X‐ray crystallography plays a vital role in their identification.</jats:p>

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詳細情報 詳細情報について

  • CRID
    1872835442851052032
  • DOI
    10.1002/poc.4454
  • ISSN
    10991395
    08943230
  • データソース種別
    • OpenAIRE

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