Compaction of Organometallic Reactions

2014 Fiscal Year Final Research Report

• Project Area: Organic Synthesis based on Integration of Chemical Reactions. New Methodologies and New Materials
• Project/Area Number: 21106004
• Research Category: Grant-in-Aid for Scientific Research on Innovative Areas (Research in a proposed research area)
• Allocation Type: Single-year Grants
• Review Section: Science and Engineering
• Research Institution: Okayama University of Science
• Principal Investigator: ORITA Akihiro 岡山理科大学, 工学部, 教授 (30262033)
• Project Period (FY): 2009-04-01 – 2015-03-31
• Keywords: 環状アセチレン / スルホン / 脱離 / ワンポット / 求核付加 / 求電子付加

Outline of Final Research Achievements

Highly strained cyclic acetylenes, Sondheimer-Wong diynes having various substituents on their benzene rings could be synthesized by one-pot treatment of the corresponding formylsulfones with diethyl chlorophosphate/lithium hexamethyldisilazide (LiHMDS) and lithium diisopropylamide (LDA). When a mixture of two types of formylsulfones bearing different substituents were subjected to this protocol, the unsymmetrically substituted Sondheimer-Wong diynes could be synthesized in a stepwise manner; the isolation of hetero-coupling vinylsulfone intermediates followed by their treatment with LDA. The UV-vis absorption spectra and cyclic voltammetries of the substituted Sondheimer-Wong diynes were recorded. The electronic effect of substituents on the diynes was investigated in their click reaction and nucleophilic and electrophilic additions.

Free Research Field

有機化学