CYCLIALKYLATION STUDIES .3. ACID-CATALYZED CYCLODEHYDRATION OF SOME BENZYLTETRALOLS, WITH AND WITHOUT REARRANGEMENT, TO YIELD TETRACYCLIC HYDROCARBONS

被引：6

作者：

PRASAD, RS ^{[1
]}

ROBERTS, RM ^{[1
]}

机构：

[1] UNIV TEXAS,DEPT CHEM,AUSTIN,TX 78712

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 09期

关键词：

D O I：

10.1021/jo00009a013

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Acid-catalyzed cyclodehydration of some benzyltetralols has been used to prepare tetracyclic hydrocarbons as synthons for compounds of potential pharmacological value. Upon treatment with sulfuric acid at 25 or 40-degrees-C, 4-benzyl-2-tetralol (15) gave a 70:30 mixture of 2,3:6,7-dibenzobicyclo[3.2.2]nona-2,6-diene (7) and 2,3:6,7-dibenzobicyclo[3.3.1]nona-2,6-diene (8). Reaction of 15 with p-toluenesulfonic acid in refluxing cyclohexane solution gave the same two products (7 and 8) as well as a small amount of 1-benzyl-1,2-dihydronaphthalene (16). Treatment of either 15 or 16 with AlCl3 gave only 8. Treatment of 1-benzyl-2-tetralol (17) with AlCl3 also gave 8. The mechanism of formation of 7 and 8 from 15 and 16 is discussed.

引用

页码：2998 / 3000

页数：3

共 26 条

[1] SYNTHESIS OF POLYCYCLIC COMPOUNDS .5. THE CYCLODEHYDRATION OF 3-BENZYCYCLOHEXANOL [J].