Friedel-Crafts Alkylation

The Friedel-Crafts Alkylation reaction is used to add an alkyl group to an aromatic ring in the presence of a strong lewis acid.  This reaction was developed by Charles Fiedel (France) and James Crafts (USA) in 1876, in studying reactions involving the creation of carbon-carbon bonds, some of the most valuable technology in organic chemistry.

This reaction involves taking an aromatic ring and adding an alkyl halide (Cl-R1) with a strong lewis acid (AlCl₃), where the alkyl halide can exist as a tri-substituted, all the way to a methyl.  The chemistry of this reaction involves the AlCl₃ to strip the Cl from the alkyl halide, forming a carbocation (R⁺), followed with the π electrons of the aromatic ring to grab the carbocation. The AlCl₄^- can now strip the H away from the position where the R added on the aromatic ring, reverting the catalyst back to it's original form, and the final product to be formed.

3/17/2012 - Barbier and the Grignard Reactions

    And once again I apologize for my prolonged absence from the blog as with my injury it induces pain that lasts for a good period of time, and then it lets off for a couple days, only to drive right back into the pain.  Some of these times, I really can't find it in me to do a blog post even though I have so much free time condemned to me.
    As the organometallic history progressed, in 1899, a man by the name of P. Barbier investigated reactions involving an alkyl halide being used as an addition reaction onto strongly electrophilic points.  These reactions were usually involving using reactants such as: an alkyl halide, Zinc, and followed by an aqueous work up.  He began studies focused on finding other metals that could have similar use in these kinds of reactions.  He concluded that adding Magnesium instead of Zinc consequented in a more efficient addition.  His student Grignard followed up by effectively describing the reaction in more detail resulting in the reaction being named after him and also with winning the Nobel Prize.

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1/25/2012 - Activation and Functionalization of a Linear Alkane through Tungsten Complex

    Here is another reaction involving the activation of a carbon hydrogen bond where after the activation the alkane can be functionalized through the addition of iodine into the system under liquid nitrogen.  The study was performed out of my home department of chemistry at the University of British Columbia done by Peter Legzdins, Jenkins Y.K. Tsang, and Miriam S.A. Buschhaus in 2007.  The tungsten complex was particularly a tungsten allyl nitrosyl complex, which allows the linear ƞ3 alkane to be attacked by the I2 in creating the selective alkyl halide at the terminal position (1-iodopentane here specifically).

Image: From source
Source: J. AM. CHEM. SOC. 2007, 129, 5372-5373