期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 350, 期 9, 页码 1376-1382出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200800088
关键词
alcohols; aldehydes; allenes; electrophilic addition; halogens; ketones
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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