Application of [Hydroxy(tosyloxy)iodo]benzene in the Wittig-Ring Expansion Sequence for the Synthesis of β‑Benzocyclo-alkenones from α-Benzocycloalkenones

Molecules

Michael W. Justik¹ 

[1] id="af1-molecules-10-00217">Department of Chemistry, The University of Akron, Akron, Ohio, 44325. USA. Tel.: [phone], Fax: [phone]

关键词: [Hydroxy(tosyloxy)iodo]benzene;    benzocycloalkenones;    ring expansion;    oxidative rearrangement;   

DOI  :  10.3390/10010217

来源: mdpi

【 摘 要 】

The conversion of α-benzocycloalkenones to homologous β-benzocyclo-alkenones 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 alternative to analogous sequences in which Tl(NO₃)₃·3H₂O or the Prevost combination (AgNO₃/I₂) are employed in the oxidation step.

【 授权许可】

Unknown   
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