Lithium (3,3-Dimethyl-1-butynyl)vinylcuprate

[41602-03-3]  · C8H12CuLi  · Lithium (3,3-Dimethyl-1-butynyl)vinylcuprate  · (MW 178.69)

(mixed cuprate vinyl transfer agent)

Alternate Name: lithium (t-butylethynyl)vinylcuprate.

Preparative Methods: prepared in situ by addition of Vinyllithium to 3,3-Dimethyl-1-butynylcopper(I) in ether at -40 °C.1

Handling, Storage, and Precautions: air- and moisture-sensitive. Use in a fume hood.

Vinyl Transfer Agent.

Lithium (3,3-dimethyl-1-butynyl)vinylcuprate (1) is thermally more stable than Lithium Divinylcuprate and has been shown to transfer the vinyl group preferentially in 1,4-addition to enones (eq 1). Reaction of (1) with isophorone (2) is sluggish but will proceed, even though partial decomposition of the cuprate was reported.1

Related Reagents.

3,3-Dimethyl-1-butynylcopper(I); Lithium (3,3-Dimethyl-1-butynyl)methylcuprate; Lithium Dimethylcuprate; Lithium Divinylcuprate.

1. House, H. O.; Umen, M. J. JOC 1973, 38, 3893.

Matthew E. Voss

The Du Pont Merck Pharmaceutical Company, Wilmington, DE, USA

Copyright 1995-2000 by John Wiley & Sons, Ltd. All rights reserved.