Studies on Electrophilic Interaction of 2,3‐Allenols with Electrophilic Halogen Reagents: Selective Synthesis of 2,5‐Dihydrofurans, 3‐Halo‐3‐alkenals, or 2‐Halo‐2‐alkenyl Ketones
2008; Wiley; Volume: 350; Issue: 9 Linguagem: Inglês
10.1002/adsc.200800088
ISSN1615-4169
AutoresJing Li, Chunling Fu, Guofei Chen, Guobi Chai, Shengming Ma,
Tópico(s)Catalytic Alkyne Reactions
ResumoAbstract The reaction of primary 2,3‐allenols with iodine (I 2 ) afforded 2,5‐dihydrofurans while that of readily available 1‐aryl or 1‐methyl substituted 2,3‐allenols with bromine (Br 2 ), N ‐bromosuccinimide (NBS), I 2 or N ‐iodosuccinimide (NIS) formed the not easily available but synthetically useful 3‐halo‐3‐alkenals and 2‐halo‐2‐alkenyl ketones with good selectivity and yields via a sequential electrophilic interaction of X + with the allene moiety, 1,2‐aryl or 1,2‐proton shift, and H + elimination process.
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