Synthesis and conformations of [2.n] metacyclophan-1-ene epoxides and their conversion to [n.1]metacyclophanes

被引：9

作者：

Akther, Thamina ^{[1
]}

Islam, Md. Monarul ^{[1
,2
]}

Rahman, Shofiur ^{[3
]}

Georghiou, Paris E. ^{[3
]}

Matsumoto, Taisuke ^{[4
]}

Tanaka, Junji ^{[4
]}

Redshaw, Carl ^{[5
]}

Yamato, Takehiko ^{[1
]}

机构：

[1] Saga Univ, Fac Sci & Engn, Dept Appl Chem, Honjo Machi 1, Saga, Saga 8408502, Japan

[2] BCSIR, Chem Res Div, Dhaka 1205, Bangladesh

[3] Mem Univ Newfoundland, Dept Chem, St John, NF A1B 3X7, Canada

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

[5] Univ Hull, Sch Math & Phys Sci, Cottingham Rd, Kingston Upon Hull HU6 7RX, Yorks, England

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2017年 / 15卷 / 16期

基金：

英国工程与自然科学研究理事会;

关键词：

MEDIUM-SIZED CYCLOPHANES; FRIEDEL-CRAFTS ACYLATION; CATALYZED REARRANGEMENT; CONVENIENT SYNTHESIS; ALCOHOLS; STEREOSELECTIVITY; DEMETHYLATION; EPOXIDATION; BBR3;

D O I：

10.1039/c7ob00400a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of syn- and anti-[2.n]metacyclophan-1-enes have been prepared in good yields by McMurry cyclizations of 1, n-bis(5-tert-butyl-3-formyl-2-methoxyphenyl)alkanes. Significantly, acid catalyzed rearrangements of [2.n]metacyclophan-1-enes afforded [n.1]metacyclophanes in good yield. The ratios of the products are strongly regulated by the number of methylene bridges present. The percentages of the rearrangement products increase with increasing length of the carbon bridges. Characterization and the conformational studies of these products are described. Single crystal X-ray analysis revealed the adoption of syn- and anti-conformations. DFT calculations were carried out to estimate the energy-minimized structures of the synthesized metacyclophanes.

引用

页码：3519 / 3527

页数：9

共 50 条

[31] SYNTHESIS OF N-HETEROCYCLES VIA CHALCONE EPOXIDES .1. AMINO AND HYDRAZINOPYRIMIDINES
OSISANYA, RA
OLUWADIYA, JO
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1989, 26 (04) : 947 - 948
[32] SYNTHESIS AND TAUTOMERISM OF 1-ARYLSULFONAMIDO-1-METHYLTHIO-2-NITROETHYLENES - CONVERSION TO N-ARYLSULFONYL NITROACETAMIDES
MAYBHATE, SP
DESHMUKH, ARAS
RAJAPPA, S
TETRAHEDRON, 1991, 47 (23) : 3887 - 3894
[33] N-ALLENYLATION OF PYRROLES WITH 2,3-DICHLOROPROP-1-ENE
TARASOVA, OA
MIKHALEVA, AI
MARKOVA, TL
TROFIMOV, BA
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1992, (01): : 125 - 125
[34] SYNTHESIS OF 2-N,N-DIALKYLAMINO-1-AROYLOXYBENZOCYCLOALKANES
HIRATA, Y
YANAGISAWA, I
TAKEDA, M
INO, H
TAKAHASHI, K
MURAKAMI, M
CHEMICAL & PHARMACEUTICAL BULLETIN, 1977, 25 (05) : 1060 - 1066
[35] RNS Comparison via Shortcut Mixed Radix Conversion: The Case of Three 4-Moduli Sets {2 n plus k , 2 n ±1,m} (m∈{2 n+1±1, 2 n-1-1})
Torabi, Z.
Jaberipur, G.
Mirnaseri, S. A.
IETE JOURNAL OF RESEARCH, 2023, 69 (05) : 2567 - 2573
[36] Breaking the 2n-bit carry propagation barrier in residue to binary conversion for the [2n-1, 2n, 2n+1] modula set
Bhardwaj, M
Premkumar, AB
Srikanthan, T
IEEE TRANSACTIONS ON CIRCUITS AND SYSTEMS I-FUNDAMENTAL THEORY AND APPLICATIONS, 1998, 45 (09): : 998 - 1002
[37] Synthesis and crystal structures of new complexes of di- and tribenzyltin N-ethyl and N-benzyl-2-amino cyclopent-1-ene-1-carbodithioates
Tarassoli, A
Asadi, A
Hitchcock, PB
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 645 (1-2) : 105 - 111
[38] Synthesis and structural features of copper(II) complexes of N,N,N′,N′-tetramethylethylenediamine with 2-chlorobenzoate1- and 2-hydroxybenzoate1-
Batool, Syeda Shahzadi
Gilani, Syeda Rubina
Tahir, Muhammad Nawaz
Harrison, William T. A.
Mitu, Liviu
Mazharr, Sania
JOURNAL OF COORDINATION CHEMISTRY, 2018, 71 (16-18) : 2569 - 2583
[39] Pyrolysis of dimethoxy[n.2]metacyclophanes: an intramolecular condensation reaction to give oxa[n.2.1](1,3,2)cyclophanes
Do, Jung-Hee
Yamada, Yuta
Sharma, Bigyan
Yamato, Takehiko
JOURNAL OF CHEMICAL RESEARCH, 2012, (03) : 134 - 137
[40] Demethylation of 5,n-di-tert-butyl-8,n-dimethoxy[2.n] metacyclophane-1-ynes with BBr3 to afford novel [n] benzofuranophanes
Akther, Thamina
Islam, Md Monarul
Matsumoto, Taisuke
Tanaka, Junji
Feng, Xing
Redshaw, Carl
Yamato, Takehiko
JOURNAL OF MOLECULAR STRUCTURE, 2016, 1122 : 247 - 255

← 1 2 3 4 5 →