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

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

Jr *  and
Instituto de Química, Universidade de São Paulo, Av. Prof. Lineu Prestes, 748. CP 26077, CEP 05513- 970, São Paulo, Brazil
* Author to whom correspondence should be addressed.
Received: 24 March 2005 / Revised: 26 July 2005 / Accepted: 26 July 2005 / Published: 30 November 2005
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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. Thallium(III); ring contraction; dimethoxylation; homoallylic alcohols.
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.

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

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