Advertisement

If you have an ACS member number, please enter it here so we can link this account to your membership. (optional)

ACS values your privacy. By submitting your information, you are gaining access to C&EN and subscribing to our weekly newsletter. We use the information you provide to make your reading experience better, and we will never sell your data to third party members.

ENJOY UNLIMITED ACCES TO C&EN

Synthesis

Unique C-H Activation

May 7, 2007 | A version of this story appeared in Volume 85, Issue 19

A new allyl nitrosyl complex of tungsten selectively activates the terminal C-H bond of linear alkanes under ambient conditions in a new way that could prove useful in chemical syntheses (J. Am. Chem. Soc. 2007, 129, 5372). The complex (structure on left) is thermally unstable, losing neopentane [C(CH3)4] at 20 °C by abstracting a hydrogen atom from the allyl ligand. The intermediate diene complex (center) then reacts with the alkane solvent—in this case, n-pentane—to add an n-pentyl ligand, essentially hiding the displaced terminal hydrogen within the diene ligand to restore the allyl ligand. The n-pentyl complex (right) can react with I2 to yield 1-iodopentane, the starting point for further derivatizations. "The most intriguing aspect of this chemistry," notes Peter Legzdins of the University of British Columbia, in Vancouver, who led the research, "is that the C-H bond activation yields a thermally stable—and isolable&mdah;allyl complex instead of a thermally unstable hydrido alkyl complex."

Article:

This article has been sent to the following recipient:

0 /1 FREE ARTICLES LEFT THIS MONTH Remaining
Chemistry matters. Join us to get the news you need.