ISSN:
0009-2940
Keywords:
Fiscellanes, doubly-bridged
;
Semibullvalenes, doubly-bridged
;
Cyclopropanes
;
SEM-protective groups
;
Annulenes
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Synthesis and Reactions of the First Doubly-Bridged FiscellanesThe 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.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19941270515
