A Novel Catalytic Effect of Lead on the Reduction of a Zinc Carbenoid with Zinc Metal Leading to a Geminal Dizinc Compound. Acceleration of the Wittig-Type Olefination with the RCHX2-TiCl4-Zn Systems by Addition of Lead

Kazuhiko Takai; Tadahiro Kakiuchi; Yasutaka Kataoka; Kiitiro Utimoto

doi:10.1021/jo00089a002

A Novel Catalytic Effect of Lead on the Reduction of a Zinc Carbenoid with Zinc Metal Leading to a Geminal Dizinc Compound. Acceleration of the Wittig-Type Olefination with the RCHX₂-TiCl₄-Zn Systems by Addition of Lead

Kazuhiko Takai, Tadahiro Kakiuchi, Yasutaka Kataoka, Kiitiro Utimoto

Research output: Contribution to journal › Article › peer-review

251 Citations (Scopus)

Abstract

A catalytic amount of lead promotes further reduction of zinc carbenoid (ICH₃ZnI) with zinc in THF to give a geminal dizinc compound (CH₂(ZnI)₂), which is a key intermediate for the methylenation of carbonyl compounds with a CH₂I₂, zinc, and TiCl₄ system.

Original language	English
Pages (from-to)	2668-2670
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	59
Issue number	10
DOIs	https://doi.org/10.1021/jo00089a002
Publication status	Published - May 1 1994

ASJC Scopus subject areas

Organic Chemistry

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A Novel Catalytic Effect of Lead on the Reduction of a Zinc Carbenoid with Zinc Metal Leading to a Geminal Dizinc Compound. Acceleration of the Wittig-Type Olefination with the RCHX₂-TiCl₄-Zn Systems by Addition of Lead. / Takai, Kazuhiko; Kakiuchi, Tadahiro; Kataoka, Yasutaka et al.
In: Journal of Organic Chemistry, Vol. 59, No. 10, 01.05.1994, p. 2668-2670.

Research output: Contribution to journal › Article › peer-review

Takai, K, Kakiuchi, T, Kataoka, Y & Utimoto, K 1994, 'A Novel Catalytic Effect of Lead on the Reduction of a Zinc Carbenoid with Zinc Metal Leading to a Geminal Dizinc Compound. Acceleration of the Wittig-Type Olefination with the RCHX₂-TiCl₄-Zn Systems by Addition of Lead', Journal of Organic Chemistry, vol. 59, no. 10, pp. 2668-2670. https://doi.org/10.1021/jo00089a002

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abstract = "A catalytic amount of lead promotes further reduction of zinc carbenoid (ICH3ZnI) with zinc in THF to give a geminal dizinc compound (CH2(ZnI)2), which is a key intermediate for the methylenation of carbonyl compounds with a CH2I2, zinc, and TiCl4 system.",

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