Efficient synthesis of cyclic β-oxophosphoranes by microwave-assisted reaction of cyclic phosphine oxides and dialkyl acetylenedicarboxylates

被引:34
作者
Keglevich, G [1 ]
Dudas, E
Sipos, M
Lengyel, D
Ludanyi, K
机构
[1] Budapest Univ Technol & Econ, Dept Organ Chem Technol, H-1521 Budapest, Hungary
[2] Semmelweis Univ, Fac Pharm, Dept Pharmaceut, H-1092 Budapest, Hungary
[3] Hungarian Acad Sci, Chem Res Ctr, H-1525 Budapest, Hungary
来源
SYNTHESIS-STUTTGART | 2006年 / 08期
关键词
cyclic phosphine oxides; alkyne derivatives; inverse-Wittig reactions; phosphoranes; ylides; microwave synthesis;
D O I
10.1055/s-2006-929395
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The inverse Wittig-type reaction of a series of 2,4,6-trialkylphenyl cyclic phosphine oxides 3, 5, 7, 9, 11, 13, 15, 18 and 20 and dialkyl acetytenedicarboxylate giving beta-oxophosphoranes 4, 6, 8, 10, 12, 14, 16, 19 and 21, respectively, can be accomplished in a convenient way under microwave conditions. At 150 degrees C, the MW-assisted reaction is more efficient and becomes 50-fold faster as compared to the thermal transformation. A further advantage is that the 2,5-dihydrophosphole moiety of the 2,4,6-triisopropylphenyl derivative 3 does not undergo double-bond rearrangement and that the 2,4,6-trimethylphenyl substrates 11 and 13, otherwise inactive in the reaction under discussion, Could also be converted to beta-oxophosphoranes 12 and 14. A series of new products 4Bb, 12, 14, 16b, 19 and 21 have been made available.
引用
收藏
页码:1365 / 1369
页数:5
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