α-Iodoalkyl-Iodine-Ate Complexes as Observable Intermediates in the Iodine- Magnesium Exchange Reaction

Volker Schulze; Mark Brönstrup; Volker P W Böhm; Peter Schwerdtfeger; Michael Schimeczek; Reinhard W Hoffmann

doi:10.1002/(SICI)1521-3773(19980403)37:6<824::AID-ANIE824>3.0.CO;2-6

α-Iodoalkyl-Iodine-Ate Complexes as Observable Intermediates in the Iodine- Magnesium Exchange Reaction

Angew Chem Int Ed Engl. 1998 Apr 3;37(6):824-826. doi: 10.1002/(SICI)1521-3773(19980403)37:6<824::AID-ANIE824>3.0.CO;2-6.

Authors

Volker Schulze¹, Mark Brönstrup¹, Volker P W Böhm¹, Peter Schwerdtfeger¹, Michael Schimeczek¹, Reinhard W Hoffmann¹

Affiliation

¹ Fachbereich Chemie der Universität, Hans-Meerwein-Strasse, D-35032 Marburg (Germany), Fax: (+49) 6421-28-8917.

PMID: 29711393
DOI: 10.1002/(SICI)1521-3773(19980403)37:6<824::AID-ANIE824>3.0.CO;2-6

Abstract

An intermediate with a half-life of 30 minutes has been observed in the iodine-magnesium exchange reaction of 1,1-diiodoalkanes in THF at -78°C. This intermediate is likely the ate complex 1. Its characteristic chemistry calls for a mechanistic reconsideration of several features of the halogen-metal exchange reaction.

Keywords: Ate complexes; Carbenoids; Hypervalent compounds; Iodine; Metalations.