摘要
研究了1-和2-苯基萘,1,1’-和2,2’-联萘,2,2-二羟基-,2,2’-二甲氧基和-2,2’-二甲磺酰氧基-1,1’-联萘等七种萘衍生物和三氧化硫的磺化反应。1-苯基萘和1,1’-联萘的磺化先发生在4位上,第二取代位置为6和7位。2-苯基萘和2,2’-联萘均首先得到8位磺酸取代物,进一步磺化得到8,4’-和8,8’-二磺酸取代物。2,2’-二甲氧基-1,1’-联萘以13:87的比例得到3位和6位磺酸取代物。2,2’-二甲磺酰氧基-1,1’-联萘以58:42的比例得到5位和6位磺酸取代物。2,2’-二羟基-1,1’-联萘的等摩尔磺化得到比例为35:65的5位和6位磺酸取代物,和大于6摩尔的SO_3反应则以62:38的比例得到5位和6位磺酸取代物。
Sulfonation of 1- and 2-phenylnaphthalene, 1, 1'-binaphthyl, 2, 2'-dihydroxy, 2,2'-dimethoxy and 2,2' -dimethoxy derivatives of 1,1' -binaphthyl with SO3 in dichloromethane as solvent was studied. Sulfonation of 1-phenylnaphthalene and 1, 1'-binaphthyl leads to substitution at the 4-position and subsequently at the 6- and 7-position. Upon Sulfonation the more planar 2-phenylnaphthalene and 2, 2 '-binaphthyl both give initially the 8-sulfonic acid derivative and subsequently a mixture of 8, 4'- and 8,8'-disulfonic acid derivative. Sulfonation of 2, 2'-dimethoxy-1, 1'-binaphthyl gives initiall the 3- and 6-sulfonic acid derivatives in an isomer ratio of aproximately 13-' 87, monosulfonation of 2,2'-dimesyloxy-1, 1 '-binaphthyl gives the 5- and 6-sulfonic acid derivative in a ratio of 58:42. Sulfonation of 2, 2'-dihydroxy-1, 1'-binaphthyl gives initially the 5- and 6-solfonic acid derivative, the ratio of which increases upon increasing the amount of SO3 employed from approximately 35:65 on using≤1.0 mol. of SO3 to approximately 62 : 38 on using >6.0 mol. of SO3.
出处
《有机化学》
SCIE
CAS
CSCD
北大核心
1996年第4期349-356,共8页
Chinese Journal of Organic Chemistry
基金
国家教委回国人员科研经费资助项目
关键词
联萘
衍生物
三氧化硫
磺化反应
binaphthyl derivative, sulfo trioxide, aromatic sulfnation