First Evidence for the Formation of a Geminal Dizinc Carbenoid:  A Highly Stereoselective Synthesis of 1,2,3-Substituted Cyclopropanes

• Published in: Journal of the American Chemical Society Vol. 124; no. 3; pp. 386 - 387
• Main Authors: Charette, André B, Gagnon, Alexandre, Fournier, Jean-François
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 23.01.2002; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Multidisciplinary; Cyclopropanes - chemical synthesis; Exact sciences and technology; Kinetics and mechanisms; Organic chemistry; Physical Sciences; Reactivity and mechanisms; Science & Technology; Stereoisomerism; HALIDES; REACTIVITY; ZINC REAGENTS; ORGANOBISMETALLIC REAGENTS; CYCLIC STEREOCONTROL; Zinc Organic compounds; Cyclopropanation; Reaction intermediate; Stereoselectivity; Organic free biradical; Carbenoid; Experimental study; Ethylenic compound; Primary alcohol

Significant amounts of novel gem-dizinc carbenoids (RZnCHIZnR) are formed when diethylzinc is mixed with iodoform in CH2Cl2 at 0 °C. This reagent was shown to be effective in the cyclopropanation of butenediol derivatives to generate a cyclopropylzinc intermediate that could be trapped with a variet...