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Synthese und Reaktionen der ersten zweifach überbrückten Fiscellane
Author(s) -
Düll Bernhard,
Müllen Klaus
Publication year - 1994
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19941270515
Subject(s) - chemistry , sodium iodide , derivative (finance) , diol , iodide , acetone , chloride , stereochemistry , medicinal chemistry , polymer chemistry , organic chemistry , financial economics , economics
Synthesis and Reactions of the First Doubly‐Bridged Fiscellanes The synthesis of the novel hexacycle 2 containing a fiscellane framework is described. Starting from Weiss' tetraester 6 , the fiscellane 2 is build up in six steps by successive chemical transformation of the methoxycarbonyl functions using SEM protecting groups. The behaviour of the novel diol 2 towards introduction of several leaving groups is examined. Upon treatment with methanesulfonyl chloride the highly strained hexacycle 2 undergoes a skeletal rearrangement with formation of the triene 4 . Instead of reacting to a doubly‐bridged semibullvalene 3 , the diol 2 gives rise to a new heterocyclic π perimeter 5 when the trifluoroacetyl derivative 12 is treated with sodium iodide in acetone.