Unexpected SN2′-type addition-elimination reactions of 1-aryl-2,3-allenols with LiX.: Synthesis and synthetic application of 1-aryl-3-halo-1,3-dienes

被引：34
作者：
Ma, SM [1 ]
Wang, GW [1 ]
机构：
[1] Acad Sinica, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
来源：
TETRAHEDRON LETTERS | 2002年 / 43卷 / 33期
基金：
中国国家自然科学基金;
关键词：
allenes; alcohols; substitution; dienes;
D O I：
10.1016/S0040-4039(02)01207-8
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
1-Aryl-3-halo-1,3-dienes were prepared from the sequential addition-elimination reaction of 1-aryl-2,3-allenols with LiX (X = Br, Cl) in HOAc in moderate to good yields. Here the aromatic substituent is crucial to this interesting transformation since no reaction was observed with 1-alkyl or perfluoroalkyl-2,3-allelols. The 1-aryl-3-halo-1,3-dienes prepared can be used as Useful partners in Diels-Alder reactions with dienophiles leading to polycyclic quinone derivatives, (C) 2002 Elsevier Science Ltd. All rights reserved.
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收藏
页码：5723 / 5726
页数：4
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