SOLVOMERCURATION-DEMERCURATION OF LIMONENE WITH HG(BF4)2 - A CHEMOSPECIFIC AND REGIOSPECIFIC ROUTE TO 8-SUBSTITUTED PARA-MENTHENES

被引:9
作者
DEMATTOS, MCS
KOVER, WB
AZNAR, F
BARLUENGA, J
机构
[1] UNIV FED RIO DE JANEIRO,INST QUIM,DEPT QUIM ORGAN,BR-21945 RIO DE JANEIRO,BRAZIL
[2] UNIV ESTADO RIO DE JANEIRO,INST QUIM,DEPT QUIM ORGAN,BR-20551 RIO DE JANEIRO,BRAZIL
[3] UNIV OVIEDO,FAC QUIM,DEPT QUIM ORGANOMET,E-33071 OVIEDO,SPAIN
关键词
LIMONENE; MERCURATION-DEMERCURATION; ALPHA-TERPINEOL; MERCURIC TETRAFLUOROBORATE; PARA-MENTHENES;
D O I
10.1016/S0040-4039(00)61218-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Solvomercuration-demercuration of limonene with equimolar Hg(BF4)2 and excess nucleophile (-20-degrees-C) functionalizes the acyclic double bond and provides specifically 8-substituted p-menthenes.
引用
收藏
页码:4863 / 4866
页数:4
相关论文
共 11 条
[1]   OXYMERCURATION-DEMERCURATION OF LIMONENE [J].
BAMBAGIOTTI, MA ;
VINCIERI, FF ;
CORAN, SA .
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (05) :680-682
[2]   UNEXPECTED BEHAVIOR OF LIMONENE IN THE OXIDATIVE AMINOMERCURATION REACTION WITH HGO/HBF4 AND AROMATIC-AMINES - STEREOSPECIFIC SYNTHESIS OF 1,2-DIAMINES [J].
BARLUENGA, J ;
AZNAR, F ;
DEMATTOS, MCS ;
KOVER, WB ;
GARCIAGRANDA, S ;
PEREZCARRENO, E .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (08) :2930-2932
[3]  
BARLUENGA J, 1979, SYNTHESIS-STUTTGART, P962
[4]   SOLVOMERCURATION-DEMERCURATION .4. MONOHYDRATION OF REPRESENTATIVE DIENES VIA OXYMERCURATION-DEMERCURATION [J].
BROWN, HC ;
GEOGHEGA.PJ ;
LYNCH, GJ ;
KUREK, JT .
JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (12) :1941-&
[5]   OXYMERCURATION-DEMERCURATION OF REPRESENTATIVE OLEFINS . A CONVENIENT MILD PROCEDURE FOR MARKOVNIKOV HYDRATION OF CARBON-CARBON DOUBLE BOND [J].
BROWN, HC ;
GOEGHEGA.P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (06) :1522-&
[6]  
Buckingham J., 1996, DICT ORGANIC COMPOUN
[7]   ULTRASOUND IN ORGANIC-SYNTHESIS .18. SELECTIVE OXYMERCURATION VIA SONOCHEMICALLY INSITU GENERATED MERCURY SALTS [J].
EINHORN, J ;
EINHORN, C ;
LUCHE, JL .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (19) :4479-4481
[8]  
FREUDENBERG K, 1955, LIEBIGS ANN CHEM, V594, P76
[9]  
LAROCK RC, 1986, SOLVOMERCURATION REA
[10]   HYDROXYMERCURATION OF NONCONJUGATED DIENES IN AQUEOUS MICELLES [J].
LINK, CM ;
JANSEN, DK ;
SUKENIK, CN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (26) :7798-7799