2-Halo-2-cyclohexenols from 6,6-Dihalobicyclo-[3.1.0]hexanes and Dimethyl Sulfoxide. Studies towards a Non-basic Hydroxide Equivalent.

Syntheses ofgem-Dihalocyclopropanes and Their Use in Organic Synthesis

“…2-Halo-2-cycloalkenols were prepared by heating some n,n-dihalobicyclo[n-3.1.0]alkanes in DMSO. 378 Intermediate 1,n-dihalocycloalkenes were formed and underwent nucleophilic attack by DMSO, followed by a Pummerer rearrangement and hydrolytic decomposition (eq 102).…”

Anti-Friedel-Crafts-Type Substitution To Form Biaryl Linkages

“…Acetylation to 8 and bromination in the presence of N-bromosuccinimide following classical protocols led to the first key intermediate, the 4′-bromo compound 2 in 76% yield overall. Treatment with dimethyl sulfoxide, depending on the conditions, can directly give either 1, 14 or the aldehyde 9 (Kornblum oxidation) that can be reduced in one step to the biphenylic congener 1 of Fréchet's building units in 92% yield.…”

Electrocyclic Ring-Opening Reactions of gem-Dibromocyclopropanes in the Synthesis of Natural Products and Related Compounds

“…Sandler 72 found that the parent underwent hydrolytic ring cleavage with various Ag(I) salts to give 2-bromocyclohexen-3-ol or its derived acetate, but the group of Wesserjohann 102 have now found that yields of up to 95% of the alcohol can be attained simply by performing the reaction in DMSO-water. It has been suggested that the oxygen of DMSO acts as nucleophile (Scheme 39).…”