96362-89-9Relevant academic research and scientific papers
E/Z isomerism without a double bond - An unusual type of stereoisomerism, and an unprecedented isomerisation in a bicyclobutane
Ruecker, Christoph,Haftstein, Gunter
, p. 237 - 241 (2007/10/03)
An unusual kind of stereoisomerism termed E/Z isomerism without a double bond or generalised E/Z isomerism is discussed for the first time. Examples are given of pairs of synthesized and separated compounds related by this kind of isomerism (4a/5a and 12a/15a), which were obtained by an unusual rearrangement of substituents on a bicyclobutane ring system. Conditions for the occurrence of generalised E/Z isomerism are defined.
Phenylsulphonyl-Substituted Octabisvalenes. - Syntheses and Reactions
Ruecker, Christoph
, p. 1629 - 1644 (2007/10/02)
(Z)-3,7-Bis(phenylsulphonyl)octabisvalene (2), the first derivative of octabisvalene, is synthesized in an eleven-step sequence starting from cis-benzene trioxide.The six new C-C bonds are formed by inter- and intramolecular nucleophilic substitutions at all six C atoms of the starting material.An improved synthesis (shortened to eight steps) yields preparatively useful quantities of 2.Bromine or monovalent nucleophiles add to one of the two bicyclobutane units in 2; the tetracyclo2,4.03,5>octanes of type 32-34, 38-41 obtained do not undergo further addition.Addition to both bicyclobutane systems is achieved intramolecularly by divalent nucleophiles, yielding bridged tricyclo2,4>octanes of type 42/45.Lithation and silylation of 2 as well as reductive removal of the sulphonyl groups give rise to other substituted octabisvalenes (46-54,56), among them to the monosubstituted 3-(phenylsulphonyl)octabisvalene (51).
