New preparation of 1,2,4,5-tetraoxanes

被引:66
作者
Terent'ev, AO
Kutkin, AV
Starikova, ZA
Antipin, MY
Ogibin, YN
Nikishina, GI
机构
[1] Russian Acad Sci, ND Zelinskii Organ Chem Inst, Moscow 119991, Russia
[2] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 119991, Russia
来源
SYNTHESIS-STUTTGART | 2004年 / 14期
关键词
tetraoxanes; heterocycles; peroxides; acetals; boron;
D O I
10.1055/s-2004-831171
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A convenient procedure was developed for the synthesis of 1,2,4,5-tetraoxanes based on the reaction of gem-bishydroperoxycycloalkanes with ketals and acetals catalyzed by boron trifluoride etherate, which makes it possible to prepare the target products in yields from 13 to 93%.
引用
收藏
页码:2356 / 2366
页数:11
相关论文
共 59 条
[1]   ONE ELECTRON-TRANSFER CHAIN DECOMPOSITION OF TRIFLUOROACETONE DIPEROXIDE - THE 1ST 1,2,4,5-TETROXANE WITH O-TRANSFER CAPABILITY [J].
ADAM, W ;
ASENSIO, G ;
CURCI, R ;
MARCO, JA ;
GONZALEZNUNEZ, ME ;
MELLO, R .
TETRAHEDRON LETTERS, 1992, 33 (39) :5833-5836
[2]   REARRANGEMENT OF TETRAMETHYL-1,2-DIOXETANE BY BORON-TRIFLUORIDE IN APROTIC-SOLVENTS [J].
BARTLETT, PD ;
BAUMSTARK, AL ;
LANDIS, ME .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (06) :1890-1892
[3]  
Berkessel A, 2002, ANGEW CHEM INT EDIT, V41, P4481, DOI 10.1002/1521-3773(20021202)41:23<4481::AID-ANIE4481>3.0.CO
[4]  
2-7
[5]   SUBSTITUENT EFFECT ON CONFORMATIONAL MOBILITY OF CYCLIC PEROXIDES [J].
BRUNE, HA ;
WULZ, K ;
HETZ, W .
TETRAHEDRON, 1971, 27 (15) :3629-&
[6]  
CRIEGE R, 1954, CHEM BER, V87, P786
[7]  
CRIEGEE R, 1953, LIEBIGS ANN CHEM, V583, P1
[8]   NEW CYCLOTRIDECANE PEROXIDES [J].
DASNES, T ;
LEDAAL, T .
ACTA CHEMICA SCANDINAVICA, 1971, 25 (05) :1906-&
[9]  
DILTHEY W, 1940, J PRAKT CHEM, P219
[10]  
DILTHEY W, 1940, J PRAKT CHEM, P154