Alkyl substituted [2.2] paracyclophane-1,9-dienes

被引：28

作者：

Lidster, Benjamin J. ^{[1
]}

Kumar, Dharam R. ^{[1
]}

Spring, Andrew M. ^{[1
,2
]}

Yu, Chin-Yang ^{[1
,3
]}

Helliwell, Madeleine ^{[1
]}

Raftery, James ^{[1
]}

Turner, Michael L. ^{[1
]}

机构：

[1] Univ Manchester, Sch Chem, Organ Mat Innovat Ctr, Oxford Rd, Manchester M13 9PL, Lancs, England

[2] Kyushu Univ, Inst Mat Chem & Engn, 6-1 Kasuga Koen Kasuga, Fukuoka 8168580, Japan

[3] Natl Taiwan Univ Sci & Technol, Dept Mat Sci & Engn, 43,Sect 4,Keelung Rd, Taipei 10607, Taiwan

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2016年 / 14卷 / 25期

基金：

英国工程与自然科学研究理事会;

关键词：

RING-OPENING METATHESIS; BLOCK-COPOLYMERS; MILD CONDITIONS; MACRO RINGS; BENZYNE; POLYMERIZATION; POLY(P-PHENYLENEVINYLENE)S; CYCLOPHANES; POLYMERS;

D O I：

10.1039/c6ob00885b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[2.2] Paracyclophane-1,9-dienes substituted with n-octyl chains have been synthesised from the corresponding dithia[3.3] paracyclophanes using a benzyne induced Stevens rearrangement. The use of 2-(tri-methylsilyl) phenyl trifluoromethanesulfonate and tetra-n-butylammonium fluoride as the in situ benzyne source gave significantly improved yields over traditional sources of benzyne and enabled the preparation of n-octyl substituted [2.2] paracyclophane-1,9-dienes on a multi-gram scale.

引用

页码：6079 / 6087

页数：9

共 13 条

[1] Synthesis and Ring-Opening Metathesis of Tetraalkoxy-Substituted [2.2]Paracyclophane-1,9-dienes
Yu, Chin-Yang
Helliwell, Madeleine
Raftery, James
Turner, Michael L.
CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (25) : 6991 - 6997
[2] Reactivity Studies of Alkoxy-Substituted [2.2]Paracyclophane-1,9-dienes and Specific Coordination of the Monomer Repeating Unit during ROMP
Menk, Florian
Mondeshki, Mihail
Dudenko, Dmytro
Shin, Suyong
Schollmeyer, Dieter
Ceyhun, Oliver
Choi, Tae-Lim
Zentel, Rudolf
MACROMOLECULES, 2015, 48 (20) : 7435 - 7445
[3] Synthesis and ROMP of Benzothiadiazole Paracyclophane-1,9-Dienes to Donor-Acceptor Alternating Arylenevinylene Copolymers
Komanduri, Venukrishnan
Tate, Daniel J.
Marcial-Hernandez, Raymundo
Kumar, Dharam R.
Turner, Michael L.
MACROMOLECULES, 2019, 52 (18) : 7137 - 7144
[4] Synthesis and Polymerization of an ortho-para-Substituted Tetraalkoxy [2.2]Paracyclophane-1,9-diene
Mann, Arielle
Weck, Marcus
ACS MACRO LETTERS, 2022, 11 (09) : 1055 - 1059
[5] Synthesis, aggregation induced emission and through space conjugation of triphenylvinylphenyl substituted [2.2]paracyclophane-1,9-diene
Yu, Chin-Yang
Lai, Yu-Chun
RSC ADVANCES, 2018, 8 (35): : 19341 - 19347
[6] Synthesis and through-space charge transfer of dioctyloxy diperfluorohexyl substituted [22]paracyclophane-1,9-diene
Yu, Chin-Yang
Sie, Cing-Hong
Yang, Cheng-Ying
NEW JOURNAL OF CHEMISTRY, 2014, 38 (10) : 5003 - 5008
[7] RING-OPENING COPOLYMERIZATION OF [2.2]PARACYCLOPHANE-1,9-DIENE (PCPDE) AND CYCLOOCTENE (COE) - A ROUTE TO SOLUBLE PRODUCTS WITH P-PHENYLENEVINYLENE SEQUENCES
THORNCSANYI, E
KRAXNER, P
HAMMER, J
JOURNAL OF MOLECULAR CATALYSIS, 1994, 90 (1-2): : 15 - 20
[8] NEW DIENOPHILES AND DIENES .3. ON THE ADDITION OF CYANOACETYLENE TO [2.2]PARACYCLOPHANE
WITULSKI, B
ERNST, L
HOPF, H
JONES, PG
CHEMISCHE BERICHTE, 1990, 123 (10) : 2015 - 2022
[9] Bidirectional ROMP of paracylophane-1,9-dienes to tri- and penta-block p-phenylenevinylene copolymers
Komanduri, Venukrishnan
Kumar, Dharam R.
Tate, Daniel J.
Marcial-Hernandez, Raymundo
Lidster, Benjamin J.
Turner, Michael L.
POLYMER CHEMISTRY, 2019, 10 (25) : 3497 - 3502
[10] Exclusive Formation of Bridge-Substituted [2.2]Paracyclophane by Topochemical Photocycloaddition Reaction of Unsymmetrical Substituted p-Quinodimethane
Itoh, Takahito
Kondo, Fumiaki
Uno, Takahiro
Kubo, Masataka
Tohnai, Norimitsu
Miyata, Mikiji
CRYSTAL GROWTH & DESIGN, 2017, 17 (07) : 3606 - 3610

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