Safer solvents for reactive organometallic reagents Academic Article

abstract

• 2018 Elsevier Ltd This paper describes the use of poly( -olefin)s (PAOs) as safer alternatives to cyclohexane, hexanes, and heptane as solvents for alkyllithium reagents. While PAOs like any alkane are flammable, PAOs do not readily catch on fire because they contain 20 or more carbon atoms, a low volatility, and have a high flash point vis--vis alkanes like hexane. Also unlike conventional alkanes, PAOs can be quantitatively separated from polar organic solvents and polar organic products either by a simple gravity separation or by an extraction after a reaction. Any leaching of the PAO solvent into a polar phase during such a separation can be minimized by addition of small amounts of water to the polar phase. However, while these PAO solvents have some physical differences from conventional low molecular weight volatile alkanes, they otherwise behave like alkanes and alkyllithium reagents in these PAO solvents can used in their conventional reactions in these PAO solvents.

authors

• Bergbreiter, David

published proceedings

• TETRAHEDRON LETTERS

altmetric score

• 6.4

author list (cited authors)

• Malinski, T. J., & Bergbreiter, D. E.

citation count

• 5

complete list of authors

• Malinski, Thomas J||Bergbreiter, David E

publication date

• October 2018

publisher

• Elsevier  Publisher

published in

• Tetrahedron Letters: the international journal for the rapid publication of all preliminary communications in organic chemistry  Journal

keywords

• Alkyllithium Reagents
• Alternative Solvents
• Green Chemistry
• Reactive Organometallics
• Safety

Digital Object Identifier (DOI)

• 10.1016/j.tetlet.2018.09.041

start page

• 3926

end page

• 3929

volume

• 59

issue

• 44

URL

• http://dx.doi.org/10.1016/j.tetlet.2018.09.041