Electronic Character of α,3‐Dehydrotoluene Intermediates Generated from Isolable Allenyne‐Containing Substrates

Abstract: We report here the generation of α,3‐dehydrotoluenes, a relatively rare subset of reactive intermediates of the dehydroaromatic family, from isolable allenynes. The substructure motif in the allenyne substrates is distinct from, and complementary to, those found in Myers‐Saito/Schmittel‐type cycloisomerizations. The reactions reported here give rise to product profiles that provide insight about the electronic nature (i.e., diradical vs. zwitterion vs. cyclic allene) of the particular isomeric DHT (s) that is (are) produced under different reaction conditions differing most significantly in the polarity of the reaction solvent. One example also revealed previously unobserved carbene‐like reactivity of the DHT.

Location
Deutsche Nationalbibliothek Frankfurt am Main
Extent
Online-Ressource
Language
Englisch

Bibliographic citation
Electronic Character of α,3‐Dehydrotoluene Intermediates Generated from Isolable Allenyne‐Containing Substrates ; day:29 ; month:08 ; year:2022 ; extent:1
Angewandte Chemie / International edition. International edition ; (29.08.2022) (gesamt 1)

Creator
Xu, Qian
Hoye, Thomas R.

DOI
10.1002/anie.202207510
URN
urn:nbn:de:101:1-2022083015422931985683
Rights
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
Last update
15.08.2025, 7:29 AM CEST

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Associated

  • Xu, Qian
  • Hoye, Thomas R.

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