Synthesis of 2-lithio-1,3-diselenanes and 2-lithio-1,3-dithianes by Se/Li exchange: First successful trapping of axially oriented 2-lithio-1,3-diselenanes

A. Krief, L. Defrère

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Abstract

Conformationally rigid 2-methylseleno-1,3-diselenanes bearing the methylseleno moiety in axial position react with butyllithiums at low temperature (-130°C) to produce 2-lithio-1,3-diselenanes bearing the lithium in axial position. These organometallics are configurationally stable at -130°C and slowly epimerise at -78°C. Deuteration occurs exclusively from the axial side if carried out at -130°C. 2-Methylseleno-1,3-dithianes behave differently since epimerisation of 2-lithio-1,3-dithianes almost immediately takes place already at -130°C.
Original languageEnglish
Pages (from-to)8015-8018
Number of pages4
JournalTetrahedron Letters
Volume37
Issue number44
DOIs
Publication statusPublished - 28 Oct 1996

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