Premium
Vicinal Dilithioalkenes by Addition of Lithium to Simple Cyclic and Acyclic Alkynes
Author(s) -
Maercker Adalbert,
Graule Thomas,
Girreser Ulrich
Publication year - 1986
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198601671
Subject(s) - vicinal , lithium (medication) , ether , chemistry , organic chemistry , medicinal chemistry , biology , endocrinology
The use of 1,2‐dilithio(cyclo)alkenes on a preparative scale in organic synthesis is made possible by the title reaction. The addition of lithium to cyclooctyne in ether (− 35°C, 2h) results in the formation of a yellow solution of cis ‐1,2‐dilithiocyclooctene. Acyclic alkenes react much more slowly with lithium (20°C, 48 h) to give trans ‐dilithioalkenes, which are insoluble in ether.