Reaction of Thallium(III) Salts with Homoallylic Alcohols: Ring Contraction vs. Dimethoxylation

Molecules

关键词: Thallium(III);    ring contraction;    dimethoxylation;    homoallylic alcohols.;   

DOI  :  10.3390/10111419

来源: DOAJ

【 摘 要 】

The oxidation of 2-(3,4-dihydronaphthalen-1-yl)-ethanol (1) with a variety ofthallium(III) salts was investigated. An indan, formed by a ring contraction reaction, wasobtained in good to moderate yields under a variety of reaction conditions: i) thalliumtriacetate (TTA) in aqueous AcOH; ii) thallium tris-trifluoroacetate (TTFA) in aqueousTFA; iii) TTFA in CH2Cl2; iv) thallium tripropionate (TTP) in aqueous propionic acidand v) thallium tris-[(S)-(-)-triacetoxypropionate] in aqueous (S)-(-)-2-acetoxypropionicacid. On the other hand, the reaction of compound 1 with TTA in methanol led to a 2:1mixture of the corresponding cis- and trans-dimethoxylated compounds, respectively.These compounds were formed by a thallium-promoted addition of methanol to thedouble bond.

【 授权许可】

Unknown