1/29/2012 - Pharaoh's Serpent

    This reaction doesn't involve the mixing of chemicals, but instead an exothermic reaction when the compound is in contact with a significant enough heat source.  The compound needed for this reaction is Mercury (II) thiocyanate or Hg(SCN)₂, which is an incredibly toxic compound, so I advise you not to try this reaction at home, due to the toxic gases and the toxicity of the compound.  The reaction was discovered by Wohler in 1821 right after his first synthesis when he observed the winding, worm-like projections.

1/26/2012 - Synthesis of Imines from Alcohols Catalyzed by a Ruthenium Complex

     This reaction involves turning a primary alcohol into an imine product with the alleviation of hydrogen gas, catalyzed in the presence of a Ruthenium N-Heterocyclic Carbene complex in the presence of DABCO (which acts as a ligand).  The mechanism is quite complicated but it incolves the exchange of Cl's for H's onto the Ruthenium, and then the addition of the alcohol, followed by the loss of H2, and then the addition of the amine, and then the alleviation of the final imine product.  This reaction was researched by Agnese Maggi and Robert Madsen out of the Department of Chemistry at the Technical University of Denmark.

Picture: from source.

Source: Organometallics 2012, 31, 451−455

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

1/24/2012 - Oxidative Addition of the Carbon-Hydrogen Bonds of Neopentane to a Iridium(I) Complex

   In this organometallic reaction we are presented with a carbon hydrogen bond activation where the bond is cleaved.  These reactions are very important in modern chemistry as it is able to turn very cheap organic molecules into functionally expensive organic molecules.  In this reaction in particular, developed in 1982 by J.K Hoyano and W.A.G Graham out of the University of Alberta, it harnesses photochemical energy to cause an Iridium (I) organometallic complex to take up the neopentane molecule and to strip a hydrogen from the alkane.  The resulting complex contains the same number of metal carbon bonds, as there is a CO group leaving during the reaction, but there is a new Metal hydrogen bond created as the activation.

Image: Taken from source below
Source: J.K Hoyano, W.A.G Graham. J. Am. Chem. SOC. 1982, 104, 3123-3125

1/23/2012 - Biological Organometllics: Zinc protoporphyrin

   When asking someone of an example of an organometallic molecule within a human, one would usually answer with Hemoglobin, but there also exsists another within the red blood cells.  Zinc protoporphyrin is produced by the red blood cells under the conditions of lead inhibition of hemoglobin, or merely the lack of iron to produce the hemoglobin.  Because of this the presence of this molecule can act as a diagnostic tool to identify lead poisoning and a numerous number of ailments involving the red blood cells.  And when looking at the chemical structure below, it can be observed that with a simple replacement of an Iron, it can act as an oxygen carrier as there is a heme group in it.

1/22/2012 - Synthesis of Diethylzinc

     I do apologize for my lengthy absence for I had a medical complication that has unfortunately also put my education on hold, but I will promise myself to not lose my chemical knowledge due to this lengthy vacancy, so I think it is best for me to keep up this blog regularly to take my mind off the pain.  As for my first reaction back I have decided to give one that involves an organometallic (that being my passion).`  This just being a Zinc compound arranged in a linear fashion connected to two ethyl molecules creating a Diethylzinc complex.  I chose this to chow the simplicity in the synthesis of these complexes even though it exists in highly complicated bonding.  The reaction was first accomplished in 1848, and later improved to using a 1:1 mixture of ethyl bromide and ethyl iodide (both sources of an ethyl+) and an active Zinc compound such as an alloy of Zinc and Copper.

12/24/11 - Acyl Imidazolide Formation from Carboxylic Acid

    I apologize for my absence in updating this blog as I have just finished exams and I have now been frantically getting ready for Christmas while working everyday.  The reaction for this christmas eve is one that describes the synthesis of an Acid Imidazolide, which can be used in claisen like reactions due to the fact that the Imidazole acts as a good leaving group. All that is required in this reaction is to react the carboxylic acid with Carbonyl Diiamidazole (CDI), alleviating carbon dioxide and an imidazole molecule.

12/23/11 - Acyl Imidazolide Formation from Acid Chloride

   This reaction is acid imidazolide synthesis from the addition of and acid chloride to an imidazole molecule.

12/17/11 - Metal Reduction of Conjugated 2-Decalones

   As a means to regeochemically select an enolate in a decalone it is quite easy if there is a substitution at the Beta carbon.  All that is needed is a lithium solution with liquid ammonia in the presence of tert-butanol to provide protons.  These reagents create a solution of electrons which radically charge the beta position which then is pushed up to the alpha position and creating the enolate as the other negative charge is located on the oxygen, which is chelated to the lithium metal.

12/16/11 - Cyclopentadiene and Maleic anhydride

   This little snippet of a reaction was taken from an old exam for the course that I am studying for right now.  It involves a diels alder reaction between a cyclopentadiene and Maleic anhydride.  Here the diene is the cyclopentadiene (this molecule goes through diels alder reactions with itself so it is necessary to heat it above 160*C to reverse the reaction) and the dienophile as the Maleic anhydride.  This is the first step where the reaction goes as a 4π+2π endo reaction as a pericyclic reaction.  Then the second step will remove the diester as it also reduces the C=O into alcohols.  Then the final step involves turning the alkene into a 1,2-diiodine when the alkene gets halogenated, and then intramolecularly the alcohol attaches to the other point of halogenation.

12/15/11 - Sharpless Perruthenate Oxidation

   This oxidation reaction is used to turn primary or secondary alcohols into aldehydes or ketones accordingly.  The reactants involved in this reaction are the addition of (Ph3P)2RuCl2 and N-methylmorpholine-N-oxide, or also known as NMO.  What happens here is that the NMO causes the activation of the Perruthenate by oxidizing it, and then the Perruthenate continues to oxidize the alcohol which being bonded to the oxygen of the alcohol.

12/14/11 - Swern Oxidation

     Here is the second oxidation reaction, a more modern method which involves the activation of the DMSO molecule by the oxalyl chloride, which results in the addition of a chloride to the DMSO and then causes the DMSO to add to the alchohol and removing one of the alpha hydrogens.  Turning the alcohol into an aldehyde (or secondary alcohol into a ketone).