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- Title
Nitrogen‐Based Lewis Acids: Synthesis and Reactivity of a Cyclic (Alkyl)(Amino)Nitrenium Cation.
- Authors
Zhou, Jiliang; Liu, Liu Leo; Cao, Levy L.; Stephan, Douglas W.
- Abstract
Abstract: A room‐temperature‐stable crystalline cyclic (alkyl)(amino)nitrenium cation <bold>2</bold> features cationic nitrogen atom with a smaller HOMO–LUMO gap compared to that of a 1,2,3‐triazolium <bold>5</bold> (an N‐heterocyclic nitrenium cation). The low‐lying LUMO of <bold>2</bold> results in an enhanced electrophilicity, which allowed for the formation of Lewis adducts with neutral Lewis bases, such as Me3P, <italic>n</italic>Bu3P, and I<italic>i</italic>Pr. The N‐based Lewis acid <bold>2</bold> also forms an FLP with <italic>t</italic>Bu3P but subsequently reacts with (PrS)2 to cleave the S−S bond. Both experimental and theoretical results suggest that the Lewis acidity of <bold>2</bold> is stronger than its N3 analogues.
- Subjects
CRYSTALS; NITRENIUM ions; ALKYL compounds; NITROGEN; HETEROCYCLIC compounds; CHEMICAL synthesis
- Publication
Angewandte Chemie, 2018, Vol 130, Issue 13, p3380
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201713118