Synthesis and Structures of [2.n]Metacyclophan-1-enes and their Conversion to Highly Strained [2.n]Metacyclophane-1-ynes

被引：3

作者：

Akther, Thamina ^{[1
]}

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

Kowser, Zannatul ^{[1
,3
]}

Matsumoto, Taisuke ^{[4
]}

Tanaka, Junji ^{[4
]}

Rahman, Shofiur ^{[5
,6
]}

Alodhayb, Abdullah ^{[6
,7
]}

Georghiou, Paris E. ^{[5
]}

Redshaw, Carl ^{[8
]}

Yamato, Takehiko ^{[1
]}

机构：

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

[2] Bangladesh Council Sci & Ind Res BCSIR, Chem Res Div, Dhaka 1205, Bangladesh

[3] Jashore Univ Sci & Technol JUST, Dept Chem, Jashore 7408, Bangladesh

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

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

[6] King Saudi Univ, King Abdullah Inst Nanotechnol, Aramco Lab Appl Sensing Res, Riyadh 11451, Saudi Arabia

[7] King Saud Univ, Coll Sci, Dept Phys & Astron, Res Chair Tribol Surface & Interface Sci, Riyadh 11451, Saudi Arabia

[8] Univ Hull, Dept Chem & Biochem, Cottingham Rd, Kingston Upon Hull HU6 7RX, Yorks, England

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 2020卷 / 27期

基金：

英国工程与自然科学研究理事会;

关键词：

2; n]Metacyclophane-1-ynes; Strained molecules; Diels-Alder reaction; DFT calculation; MEDIUM-SIZED CYCLOPHANES; X-RAY-DIFFRACTION; ELECTROPHILIC SUBSTITUTION; CONFORMATIONAL BEHAVIOR; CONVENIENT SYNTHESIS; EXTRUSION REACTION; ARENE SYNTHESIS; ROUTE; <2.2>PARACYCLOPHANE; DEMETHYLATION;

D O I：

10.1002/ejoc.202000548

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The syntheses ofsyn-[2.n]metacyclophan-1-enes (n= 5, 6, 8) in good yields using the McMurry cyclization of 1,n-bis(3-formyl-4-methoxyphenyl)alkanes are reported. Conversion ofsyn-[2.6]- and [2.8]metacyclophan-1-enes to the corresponding highly strainedsyn-type [2.6]- and [2.8]metacyclophane-1-ynes was achieved by successive bromination and dehydrobromination reactions. An attempted trapping reaction of the putative corresponding [2.5]metacyclophane-1-yne by Diels-Alder reaction with 1,3-diphenylisobenzofuran failed due to its smaller ring size and strained structure. X-ray crystallographic analyses show that the triple bonds insyn-[2.6]- and [2.8]metacyclophane-1-ynes are distorted from linearity with bond angles of 156.7 degrees and 161.4 degrees, respectively. A DFT (Density Functional Theory) computational study was conducted to determine the stabilities of different conformations of the target compounds.

引用

页码：4167 / 4175

页数：9

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