Volume 27, Issue 16
Isocyclic Compounds
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ChemInform Abstract: Regioselective Functionalization of the Methylene Group Adjacent to Cyclopropyl Sulfide via Mercury(II)-Mediated Regioselective Ring- Opening Reaction.

Y. TAKEMOTO

Y. TAKEMOTO

Fac. Pharm. Sci., Osaka Univ., Suita, Osaka 565, Japan

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T. OHRA

T. OHRA

Fac. Pharm. Sci., Osaka Univ., Suita, Osaka 565, Japan

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Y. YONETOKU

Y. YONETOKU

Fac. Pharm. Sci., Osaka Univ., Suita, Osaka 565, Japan

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C. IWATA

C. IWATA

Fac. Pharm. Sci., Osaka Univ., Suita, Osaka 565, Japan

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First published: April 16, 1996

Abstract

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ChemInform Abstract

Regioselective cyclopropyl ring cleavage of the title sulfide (I) leads to the mercury homoallyl anion synthon (II) which can be functionalized either at the α-position to afford the iodide (IV) or at the δ-position to obtain (I) or (VI). Furthermore, oxidation and following Pummerer reaction produces the δ- oxygenated cyclopropyl sulfides (IX) and (X).

chemical structure image

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