Chemistry of silyl thioketones .9. A new selective synthesis of 1-silyl-1-enethiols and of 2-silyl-thiacycloalk-2-enes of common to large ring size.

被引:19
作者
Bonini, BF
ComesFranchini, M
Fochi, M
Mazzanti, G
Ricci, A
机构
[1] Dipto. di Chim. Organica A. Mangini, Fac. di Chimica Industriale, 40136 Bologna
关键词
D O I
10.1016/0040-4020(96)00148-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
omega-Haloacylsilanes 1 were selectively transformed via thioacylsilanes into Z-silyl-enethiols 4 with solid sodium hydrogen carbonate or into 2-silylthiacycloalk-2-ene 5 of common to large ring size with solid sodium hydroxide. Compounds 5 underwent protiodesilylation.
引用
收藏
页码:4803 / 4816
页数:14
相关论文
共 25 条
[1]   THIOALDEHYDE S-OXIDE (MONOSUBSTITUTED SULFINES) FROM THIOACYLSILANE S-OXIDES - SYNTHESIS AND FLUORINE-INDUCED AND ACID-INDUCED Z/E ISOMERIZATION .2. [J].
BARBARO, G ;
BATTAGLIA, A ;
GIORGIANNI, P ;
BONINI, BF ;
MACCAGNANI, G ;
ZANI, P .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (12) :3744-3748
[2]  
BONINI BF, 1995, SYNTHESIS-STUTTGART, P92
[3]  
BONINI BF, 1995, SYNTHESIS-STUTTGART, P261
[4]   SYNTHESIS AND ISOLATION OF ARYL THIOALDEHYDE S-OXIDES [J].
BONINI, BF ;
MAZZANTI, G ;
ZANI, P ;
MACCAGNANI, G ;
BARBARO, G ;
BATTAGLIA, A ;
GIORGIANNI, P .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (12) :964-965
[5]   CHEMISTRY OF SILYL THIOKETONES .7. SYNTHESIS, CYCLOADDITION AND OXIDATION OF CYCLOALKYL SILYL THIOKETONES AND DESILYLATION OF THE REACTION-PRODUCTS [J].
BONINI, BF ;
BUSI, F ;
DELAET, RC ;
MAZZANTI, G ;
THURING, JWJF ;
ZANI, P ;
ZWANENBURG, B .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (09) :1011-1018
[6]   CHEMISTRY OF SILYL THIOKETONES .5. SYNTHESIS AND PROPERTIES OF ALKYL ALPHA-SILYL THIOKETONES - A COMPARISON WITH ARYL DERIVATIVES [J].
BONINI, BF ;
MAZZANTI, G ;
ZANI, P ;
MACCAGNANI, G .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (11) :2083-2088
[7]   CHEMISTRY OF SILYL THIOKETONES .8. PHOTOINDUCED CYCLOADDITIONS OF SILYL THIOKETONES WITH OLEFINS [J].
BONINI, BF ;
FRANCHINI, MC ;
FOCHI, M ;
MAZZANTI, G ;
RICCI, A ;
ZANI, P ;
ZWANENBURG, B .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (16) :2039-2044
[8]   A NEW SYNTHETIC METHOD FOR 2-SILYL-THIACYCLOALK-2-ENES OF DIFFERENT RING SIZE BY INTRAMOLECULAR CYCLIZATION THROUGH SILYL THIONES [J].
BONINI, BF ;
COMESFRANCHINI, M ;
MAZZANTI, G ;
RICCI, A ;
ROSAFAUZZA, L ;
ZANI, P .
TETRAHEDRON LETTERS, 1994, 35 (49) :9227-9228
[9]   NEW CHEMISTRY WITH SILYL THIOKETONES [J].
BONINI, BF .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1993, 74 (1-4) :31-45
[10]  
BONINI BF, 1986, J CHEM SOC P1, P381