(Diacetoxyiodo)benzene‐mediated Selective Synthesis of α‐Azido Ketones or Acyl Azides from β‐Keto Acids. Issue 8 (14th June 2018)

• Record Type: Journal Article
• Authors: Zheng, Zhao‐Jing; Yu, Tian‐Yang; Xu, Peng‐Fei; Wei, Hao
• Is Part Of: Asian journal of organic chemistry. Volume 7:Issue 8(2018)
• Page Start: 1579
• Page End: 1582
• Publication Date: 2018-06-14
• Subjects: (diacetoxyiodo)benzene -- C−C bond cleavage -- organoazide compounds -- selective synthesis -- β-keto acid; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201800319
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: (Diacetoxyiodo)benzene‐mediated selective synthesis of α‐azido ketones or acyl azides from keto acids is developed. The selectivity depends on the amounts of the reagents used. Treatment of β‐keto acid derivatives with 1.2 or 2.2 equivalents of (diacetoxyiodo)benzene results in α‐azido ketone or acyl azide products, respectively. Initial mechanistic studies show that monobromomethyl ketone and dibromomethyl ketone are plausible intermediates in these reactions. Abstract : From β‐Keto to α‐azido : (Diacetoxyiodo)benzene‐mediated selective synthesis of α‐azido ketones or acyl azides from keto acids is developed. The selectivity depends on the amounts of reagents used.