NEW TRIARYLMETHYL DERIVATIVES - BLOCK GROUPS - FOR ROTAXANES AND POLYROTAXANES

被引：112
作者：
GIBSON, HW
LEE, SH
ENGEN, PT
LECAVALIER, P
SZE, J
SHEN, YX
BHEDA, M
机构：
[1] Department of Chemistry, Virginia Polytechnic Institute, State University, Blaeksburg
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 14期
关键词：
D O I：
10.1021/jo00066a030
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Five triarylcarbinols (8, three new compounds) were synthesized. Using carbanion chemistry the triarylmethanes (13, five new compounds) made by formic acid reduction of 8 were converted to the omega,omega,omega-triarylalkanols (15,three new compounds) and thence to the chloro (17) and iodo (18) derivatives (five new compounds). Via carbocation chemistry p-(triarylmethyl)phenols (20,two new compounds) and aniline (21, new compound) were produced. Alkylation of 20 yielded alcohol (22), benzylic bromide (23), and carboxy (25) functionalized derivatives. The alcohol, halide, phenol, aniline, and carboxylic acid functionalized triarylmethane compounds are suitable end blocking groups for rotaxanes and polyrotaxanes.
引用
收藏
页码：3748 / 3756
页数：9
相关论文
共 46 条
  • [1] ABBAS SA, 1948, B SOC CHIM FR, V2, P288
  • [2] SOME DIPYRIDYLALKANES
    AMES, DE
    ARCHIBALD, JL
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1962, (APR): : 1475 - &
  • [3] MOLECULAR MECCANO .1. [2]ROTAXANES AND A [2]CATENANE MADE TO ORDER
    ANELLI, PL
    ASHTON, PR
    BALLARDINI, R
    BALZANI, V
    DELGADO, M
    GANDOLFI, MT
    GOODNOW, TT
    KAIFER, AE
    PHILP, D
    PIETRASZKIEWICZ, M
    PRODI, L
    REDDINGTON, MV
    SLAWIN, AMZ
    SPENCER, N
    STODDART, JF
    VICENT, C
    WILLIAMS, DJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (01) : 193 - 218
  • [4] A NEW DESIGN STRATEGY FOR THE SELF-ASSEMBLY OF MOLECULAR SHUTTLES
    ASHTON, PR
    PHILP, D
    SPENCER, N
    STODDART, JF
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (16) : 1124 - 1128
  • [5] ASSARSON LO, 1956, ACTA CHEM SCAND, V10, P1510
  • [6] The reduction of phenyl naphthyl ketones by the binary system magnesium plus magnesium iodide
    Bachmann, WE
    Shankland, RV
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1929, 51 (1-4) : 306 - 309
  • [7] BHEDA MC, UNPUB
  • [8] BORN M, 1991, MAKROMOL CHEM-RAPID, V12, P471
  • [9] 1-TRICHLORO-2,2-BIS-(PARA-TERT-BUTYLPHENYL)-ETHANE AND DEGRADATION PRODUCTS
    CRISTOL, SJ
    HAYES, RA
    HALLER, HL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1946, 68 (05) : 913 - 914
  • [10] SYNTHESIS AND ELECTROCHEMICAL STUDIES OF CATENATES - STABILIZATION OF LOW OXIDATION-STATES BY INTERLOCKED MACROCYCLIC LIGANDS
    DIETRICHBUCHECKER, C
    SAUVAGE, JP
    KERN, JM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (20) : 7791 - 7800
12345