Structure-Reactivity Relationship in the Reaction of Highly Reactive Zinc with Alkyl Bromides

Albert Guijarro; Reuben D Rieke

doi:10.1002/(SICI)1521-3773(19980703)37:12<1679::AID-ANIE1679>3.0.CO;2-B

Structure-Reactivity Relationship in the Reaction of Highly Reactive Zinc with Alkyl Bromides

Angew Chem Int Ed Engl. 1998 Jul 3;37(12):1679-1681. doi: 10.1002/(SICI)1521-3773(19980703)37:12<1679::AID-ANIE1679>3.0.CO;2-B.

Authors

Albert Guijarro¹, Reuben D Rieke¹

Affiliation

¹ Department of Chemistry, University of Nebraska-Lincoln, Lincoln, Nebraska 68508-0304 (USA), Fax: (+1) 402-472-9402.

Abstract

Zinc is different! Unlike with magnesium or lithium, the reactions of organic bromides with highly reactive zinc (Zn*) show sensitivity for the structure of the organic moiety. Selective insertions of Zn into tertiary C-Br bonds can be achieved [Eq. (a)]. Competitive kinetic techniques were used to quantify these findings.

Keywords: Alkylations; Kinetics; Zinc.