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Reaction of Thallium(III) Salts with Homoallylic Alcohols: Ring Contraction vs. Dimethoxylation
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; in revised form: 26 July 2005 / Accepted: 26 July 2005 / Published: 30 November 2005
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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Silvia, L.F., Jr; Craveiro, M.V. Reaction of Thallium(III) Salts with Homoallylic Alcohols: Ring Contraction vs. Dimethoxylation. Molecules 2005, 10, 1419-1428.
Silvia LF, Jr, Craveiro MV. Reaction of Thallium(III) Salts with Homoallylic Alcohols: Ring Contraction vs. Dimethoxylation. Molecules. 2005; 10(11):1419-1428.
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.