1995 Fiscal Year Final Research Report Summary

Flame-induced Dimerization of Organic Compounds in Aqeous Solution

Research Project

Project/Area Number	06660126
Research Category	Grant-in-Aid for General Scientific Research (C)
Allocation Type	Single-year Grants
Research Field	Bioproduction chemistry/Bioorganic chemistry
Research Institution	University of Tsukuba
Principal Investigator	SHINYA Nomoto University of Tsukuba, Department of Chemistry, Instructor, 化学系, 講師 (30133028)
Project Period (FY)	1994 – 1995
Keywords	Flame / Radical reaction / Dimerization / Radical scavenger / sulfoxide
Research Abstract	Unsaturated amines, carboxylic acids, and amino acids were dimerized by means of the flame-induced reaction in aqueous solution. Crotonic acid afforded mainly diethylsuccinic acid among three isomers expected in this reaction, indicating that the first step of the dimerization is an addition of a hydrogen atom to the C-C double bond so as to give a more stable carbon radical. Saturated aliphatic amines and carboxylic acids were also employed as substrates and dimers were obtained in 10-20 % yields. In this case, the first step of the reaction is abstraction of a hydrogen atom from an alkyl group by a hydroxyl radical. S-Methyl cysteine sulfoxide and methionine sulfoxide afforded 2,5-diaminoadipic acid and 2,7-diaminosuberic acid, respectively, in this reaction, thought in low yields. This reaction revealed to proceed through C-S bond cleavage by the action of a hydroxyl radical.