Oxidative Desilylation of a 5,6:7,8‐Bis(dimethylsilyldioxy)[4]radialene | Zendy

Maas Gerhard | Zendy; Fronda Antonio | Zendy

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Oxidative Desilylation of a 5,6:7,8‐Bis(dimethylsilyldioxy)[4]radialene

Author(s) -

Maas Gerhard,

Fronda Antonio

Publication year - 1993

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.19931260232

Subject(s) - chemistry , salt (chemistry) , medicinal chemistry , bicyclic molecule , hydrolysis , iodine , silylation , enol , cyclobutene , ether , crystal structure , oxidative addition , silyl ether , silyl enol ether , oxidative phosphorylation , stereochemistry , catalysis , organic chemistry , ring (chemistry) , biochemistry

The title [4]radialene 1 reacts with N 1‐methyltriazolinedione or with the iodine(III) salt PhI + O + IPh · 2 BF 4 – in CH 2 Cl 2 by oxidative elimination of only one dimethylsilyl unit to form the functionalized 3,4‐bis(alkylidene)1‐1‐cyclobutene 2 or its hydrolysis products, ( Z )‐ 4 and ( E )‐ 4 . When the iodonium salt is used in CCl 4 , rearrangement of the radialene framework occurs, and the bicyclic fluorodimethylsilyl enol ether 9 is obtained. An X‐ray crystal structure analysis of 9 indicates a weak coordination between a carbonyl oxygen atom and a silyl group.

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