199807-49-3Relevant academic research and scientific papers
The synthesis of sultines from δ-hydroxy sulfoxides revisited
Connolly, Terrence J.,Durst, Tony
, p. 1337 - 1340 (2007/10/03)
A re-examination of a previously thought general synthesis of sultines from δ-hydroxy sulfoxides is shown to be more complicated than originally believed. The products obtained can be α,α'-dihaloxylenes or δ-halosulfones. The results are best interpreted based on carbocation stability of the key oxo-sulfoxonium salt intermediate.
The synthesis of bicyclic ortho-quinodimethanes from tricyclic sulfones
Connolly, Terrence J.,Durst, Tony
, p. 15957 - 15968 (2007/10/03)
The first synthesis of bicyclic ortho-quinodimethanes from tricyclic sulfone precursors has been achieved. The required sulfones, 3,4,5,6- tetrahydro-1H-cyclohex[cd]benzothiophene-2,2-dioxide and 1,3,4,5,6,7- hexahydrocyclohept[cd]benzothiophene-2,2-dioxide, were prepared from α- tetralone and benzosuberone utilizing a ring closure proceeding through a sulfonium salt intermediate. The same strategy failed when frying to prepare the tricyclic sulfone of the indane series. Other contrasting reactivity was also noticed when comparing the ability and ease of formation of tricyclic ether compounds. These results indicate that the later ring system is considerably strained.
