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
收藏
页码：3519 / 3527
页数：9
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