4.7 Article

Zwitterionic Ring-Opened Oxyphosphonium Species from the Ph3P-I2 Mediated Reactions of Benzo[d]oxazol-2(3H)-ones with Secondary Amines

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JOURNAL OF ORGANIC CHEMISTRY
卷 85, 期 9, 页码 6151-6158

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AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c00211

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  1. Chiang Mai University, Thailand
  2. Thailand Research Fund through the Royal Golden Jubilee Ph.D. Program [PHD/0072/2559]

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Instead of the expected substituted 2-aminobenzo[d]oxazoles, relatively stable ring-opened oxyphosphonium betaines were isolated for the first time from the Ph-3-P-I-2 -mediated reactions of benzo[d]oxazol-2(3H)-ones with acyclic secondary amines. The structure of one of these compounds was unambiguously confirmed by single-crystal X-ray analysis. Thermolysis of the betaines gave rise to 2-dialkylaminobenzoxazoles with concomitant loss of triphenylphosphine oxide, suggesting their possible role as intermediates in an alternative reaction path.

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