SYNTHESIS OF FURANS BY AG(I)-PROMOTED CYCLIZATION OF ALLENYL KETONES AND ALDEHYDES

被引:209
作者
MARSHALL, JA
WANG, XJ
机构
[1] Department of Chemistry, The University of South Carolina, Columbia
关键词
D O I
10.1021/jo00003a013
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of conjugated allenones (11b, 12b, 13c; 18a; 18b; 19b, 20b, AB, and 27d) were prepared by [2,3] Wittig rearrangement of (propargyloxy) acetic acids or [(progargyloxy)methy]stannanes followed by oxidation of the resultant allenylcarbinols. These allenones were readily cyclized to 2,3,5-trisubstituted furans upon treatment with AgNO3-CaCO3 in aqueous acetone. Under these conditions 2-(hydroxymethyl)-3,5-dialkylfurans self-condensed to give 2,2'-difurylmethanes.
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页码:960 / 969
页数:10
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