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Synthesis and Structure of Functionalized Zigzag Hydrocarbon Belts
Author(s) -
Zhang Yang,
Tong Shuo,
Wang MeiXiang
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202006231
Subject(s) - chemistry , hydrocarbon , zigzag , acylation , intramolecular force , ketone , nucleophile , derivative (finance) , molecule , stereochemistry , organic chemistry , geometry , catalysis , financial economics , economics , mathematics
Described in this paper are the synthesis and structure of novel and edge‐functionalized zigzag hydrocarbon belts. A stepwise “fjord‐stitching” strategy featuring repetitive intramolecular acylation reactions of a resorcin[4]arene derivative as the key steps afforded a biscarbonyl‐functionalized octahydrobelt[8]arene product. Facile ketone reduction with NaBH 4 and nucleophilic addition with n ‐butyllithium produced secondary and tertiary alcohol‐containing molecular belts, respectively. Selective oxidation reactions of biscarbonyl‐bearing octahydrobelt[8]arene with m ‐CPBA and (PhSeO) 2 O furnished the corresponding lactone‐ and 1,4‐quinone‐embedded molecular belts. Depending on the functional groups on the edges, the acquired belt molecules adopt different shapes such as square prism, truncated cone, and elliptical cylinder.