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Application of [Hydroxy(tosyloxy)iodo]benzene in the Wittig-Ring Expansion Sequence for the Synthesis of β-Benzocyclo-alkenones from α-Benzocycloalkenones
2005
Molecules
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The conversion of α-benzocycloalkenones to homologous β-benzocycloalkenones containing six, seven and eight-membered rings is reported. This was accomplished via a Wittig olefination-oxidative rearrangement sequence using [hydroxy(tosyloxy)iodo]-benzene (HTIB) is the oxidant, that enables the synthesis of regioisomeric pairs of methyl-substituted β-benzocycloalkenones. The incorporation of carbon-13 at C-1 of the β-tetralone nucleus was also demonstrated. The Wittig-HTIB approach is a useful
doi:10.3390/10010217
pmid:18007289
fatcat:5slunkhdi5cyrggg2xuk2fdv6a