Molecules 2005, 10(11), 1419-1428; doi:10.3390/10111419
Article

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

Jr * email and
Received: 24 March 2005; in revised form: 26 July 2005 / Accepted: 26 July 2005 / Published: 30 November 2005
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Abstract: 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.
Keywords: Thallium(III); ring contraction; dimethoxylation; homoallylic alcohols.
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MDPI and ACS Style

Silvia, L.F., Jr; Craveiro, M.V. Reaction of Thallium(III) Salts with Homoallylic Alcohols: Ring Contraction vs. Dimethoxylation. Molecules 2005, 10, 1419-1428.

AMA Style

Silvia LF, Jr, Craveiro MV. Reaction of Thallium(III) Salts with Homoallylic Alcohols: Ring Contraction vs. Dimethoxylation. Molecules. 2005; 10(11):1419-1428.

Chicago/Turabian Style

Silvia, Luiz F., Jr; Craveiro, Marcus V. 2005. "Reaction of Thallium(III) Salts with Homoallylic Alcohols: Ring Contraction vs. Dimethoxylation." Molecules 10, no. 11: 1419-1428.

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