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Small Hydrocarbon Cyclophanes: Synthesis, X‐ray Analysis and Molecular Modelling
Author(s) -
Lahtinen Tanja,
Wegelius Elina,
Linnanto Juha,
Rissanen Kari
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200209)2002:17<2935::aid-ejoc2935>3.0.co;2-y
Subject(s) - cyclophane , chemistry , hydrocarbon , polycyclic compound , molecule , stereochemistry , crystallography , crystal structure , organic chemistry
Small hydrocarbon cyclophanes, such as [2.2.0] m , m , m ‐cyclophane ( 20 ) and [2.2.0] p , m , m ‐cyclophane ( 21 ), are strained analogues of the well‐known π‐prismand [2.2.2] p , p , p ‐cyclophane ( 1 ). The synthetic route to these molecules is based on well‐established cyclophane methodology which offers a general access to a whole family of hydrocarbon cyclophanes. Single crystal X‐ray analysis and molecular modelling showed that the reduction of the ring size from 18‐membered ( 1 ) to 14‐membered ( 21 ) or 13‐membered ( 20 ) has a substantial effect on the size and the shape of the cyclophane’s cavity, thus blocking its ability to complex Ag + ions. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)