6) LITERATURE: A group of Japanese chemists (D. Tsuchiya, K. Moriyama, H. Togo)
ID: 853351 • Letter: 6
Question
6) LITERATURE: A group of Japanese chemists (D. Tsuchiya, K. Moriyama, H. Togo) has been publishing on creative uses of oxidation. Normally, organic chemists remove -CH2Ph (benzyl) from a nitrogen or an oxygen by reducing it off as toluene with hydrogen gas. In 2014 Togo and his group reported an oxidative way to remove a benzyl group. What was the oxidizing agent they used? What is the reference to the journal in which they reported this work? 7) LITERATURE: In 2012 that same group of Japanese researchers (Daisuke Tsuchiya, Masayuki Tabata, Katsuhiko Moriyama and Hideo Togo) found a way to make the Swern Oxidation more useful in manufacturing. The Swern oxidation evolves a stinky, toxic gas (methyl sulfide or Me-S-Me) which has been almost impossible to control in chemical factories. These Japanese chemists found a way to solve the problem of the stinky gas byproduct. What did they do? (write 2-4 lines to describe their solution). In what journal (state the full reference) did they publish this?Explanation / Answer
(6) the oxidising agent used was oxone. the other reactants were KCN , CH3CN for 24hrs reaction
the reference is
Moriyama, Katsuhiko, Yu Nakamura, and Hideo Togo. "Oxidative Debenzylation of N-Benzyl Amides and O-Benzyl Ethers Using Alkali Metal Bromide." Organic letters 16.14 (2014): 3812-3815.
(7) the scientists used ion supported methyl sulfxides to carry out swern oxidation , they treated methyl sulfoxide with ions to prepare modified methyl sulfoxides such as polyfluroalkylaed methyl sulfoxides.
swern oxidation involves methyl sulfide as a byproduct , which is a highly volatile , bad odour substance causing prolems in isolation . ion supported methyl sulfoxide was able to solve this issue producing odourless by product.
the refernce is
Tsuchiya, Daisuke, et al. "Efficient Swern oxidation and Corey