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Synthesis and chemistry of sesquibicyclo[2.2.2]octene and a tetradecacyclic-caged sesquibicyclo[2.2.2]octene

✍ Scribed by Alan P. Marchand; Sulejman Alihodžić; Eric Zhiming Dong; Simon G. Bott

Book ID
104260039
Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
217 KB
Volume
39
Category
Article
ISSN
0040-4039

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✦ Synopsis

Cationic rearrangements of functionalized spiro (norbornane-7,3'-bicyclo[2.2.2]octan-2'-ols) provide synthetic access to two novel polycarbocyclic alkenes, i.e., 5 and 10 ("sesquibicyclo[2.2.2]octene"). X-ray crystallographic analysis of 5 and 10 reveals that each alkene C=C double bond is planar in the crystalline solid. MCPBA promoted epoxidation of 5 produced the corresponding oxirane, 11. Ring opening of the highly labile oxirane moiety in 11 occurred in the presence of mild Lewis acids (e.g., silica gel) or bases (e.g., NaHCO3), thereby aflording the corresponding c/s-diol, 12. MCPBA promoted epoxidation of 7 afforded the corresponding oxirane, 13. Oxirane 13 proved to be considerably less labile than 11 toward acidic and/or basic media.

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## Abstract The substitution pattern of the 2‐phosphabicyclo[2.2.2]octene framework and the skeleton itself were varied to obtain new cycloadducts usable in phosphorylations and to study their ability to undergo fragmentation. Thus, an N‐methyl and several P‐trialkylphenyl derivatives (**__7__** an