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Development of odorless organosulfur reagents and asymmetric reaction using odorless thiols

  1. Manabu Node*,
  2. Tetsuya Kajimoto

Article first published online: 10 JUL 2007

DOI: 10.1002/hc.20348

Issue

Heteroatom Chemistry

Heteroatom Chemistry

Special Issue: ISOCS-22

Volume 18, Issue 5, pages 572–583, July 2007

Additional Information

How to Cite

Node, M. and Kajimoto, T. (2007), Development of odorless organosulfur reagents and asymmetric reaction using odorless thiols. Heteroatom Chemistry, 18: 572–583. doi: 10.1002/hc.20348

Author Information

  1. Department of Pharmaceutical Manufacturing Chemistry, 21st COE Program, Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto 607-8412, Japan

*Department of Pharmaceutical Manufacturing Chemistry, 21st COE Program, Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto 607-8412, Japan

Publication History

  1. Issue published online: 10 JUL 2007
  2. Article first published online: 10 JUL 2007
  3. Manuscript Received: 31 OCT 2006
  4. Manuscript Revised: 22 MAR 2006

Funded by

  • Ministry of Education, Culture, Sport and Technology, Japan, for Frontier Research Program, the 21st Century Center of Excellence Program “Development of Drug Discovery Frontier Integrated from Tradition to Proteome.”. Grant Number: 13470474

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Abstract

Odorless organosulfur reagents were developed by increasing their molecular weights to suppress volatility. 1-Dodecanethiol (4), dodecyl methyl sulfide (5), p-heptylphenylmethanethiol (6), p-dodecylbenzenethiol (7), p-heptylbenzenethiol (8), 2-dodecyl-1,3-propanedithiol (11), p-octyloxyphenyl-methanethiol (18b), and p-octyloxybenzenethiol (19) are typical examples of the odorless thiols and sulfides. 6-Morpholinohexyl thiol (15), methyl 6-morpholinohexyl sulfide (16), and methyl 6-morpholinohexyl sulfoxide (17) were also developed as separable reagents from reaction products by facile acid-base extraction. In addition, p-tetramethylsilylphenylmethanethiol (18) and p-tetramethylsilylbenzenethiol (14) were synthesized as the odorless synthetic substitutes of benzyl mercaptan and benzenethiol, respectively. In a similar way, silylated diphenyl disulfide (26) and diselenide (27) were prepared as odorless disulfide and diselenide. Moreover, 10-sulfanylisoborneol (1) was found to be an excellent chiral odorless substitute of hydrogen sulfide in Michael addition. © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:572–583, 2007; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20348

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