Volume 27, Issue 23
Preparative Organic Chemistry
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ChemInform Abstract: Ring Opening of Cyclopropanemonocarboxylates and 1,1- Cyclopropanedicarboxylates Using Samarium(II) Diiodide (SmI2)-HMPA-THF System.

M. YAMASHITA

M. YAMASHITA

Kyoto Pharm. Univ., Yamashinaku, Kyoto 607, Japan

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K. OKUYAMA

K. OKUYAMA

Kyoto Pharm. Univ., Yamashinaku, Kyoto 607, Japan

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T. OHHARA

T. OHHARA

Kyoto Pharm. Univ., Yamashinaku, Kyoto 607, Japan

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I. KAWASAKI

I. KAWASAKI

Kyoto Pharm. Univ., Yamashinaku, Kyoto 607, Japan

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K. SAKAI

K. SAKAI

Kyoto Pharm. Univ., Yamashinaku, Kyoto 607, Japan

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S. NAKATA

S. NAKATA

Kyoto Pharm. Univ., Yamashinaku, Kyoto 607, Japan

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T. KAWABE

T. KAWABE

Kyoto Pharm. Univ., Yamashinaku, Kyoto 607, Japan

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M. KUSUMOTO

M. KUSUMOTO

Kyoto Pharm. Univ., Yamashinaku, Kyoto 607, Japan

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S. OHTA

S. OHTA

Kyoto Pharm. Univ., Yamashinaku, Kyoto 607, Japan

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First published: June 4, 1996

Abstract

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ChemInform Abstract

SmI2 efficiently promotes the regioselective ring opening of 2- substituted cyclopropanedicarboxylates (cf. (I)) to furnish the corresponding (2-substituted ethyl)malonates (II) in moderate to high yields under optimal conditions, regardless of the type of the 2- substituent. SmI2-mediated ring opening of cyclopropanemonocarboxylates bearing an aryl group at the 2-position proceeds in a similar regioselective fashion, whilst monocarboxylates bearing an aliphatic group at C-2 do not react with SmI2 at all under the same conditions. A plausible ring opening mechanism is proposed.

chemical structure image

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