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O ‐Alkyl S ‐3,3‐Dimethyl‐2‐oxobutyl Dithiocarbonates as Versatile Sulfur‐Transfer Agents in Radical C(sp 3 )H Functionalization
Author(s) -
Sato Akinori,
Yorimitsu Hideki,
Oshima Koichiro
Publication year - 2007
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.200700251
Subject(s) - chemistry , sulfur , surface modification , alkyl , carbon atom , organic chemistry , boiling , alkane , carbon fibers , polymer chemistry , medicinal chemistry , hydrocarbon , materials science , composite number , composite material
Boiling of the title compounds in ethereal solvents or cycloalkanes in the presence of a radical initiator leads to radical C(sp 3 )H functionalization, by which a sulfur atom is introduced into the ethereal solvents at the oxygenated carbon atom or into the cycloalkanes. Both acyclic and cyclic ethers, such as [18]crown‐6 and [D 8 ]THF, undergo the sulfur transfer. The reaction is useful for the synthesis of monothioacetals, thiols, and sulfides from simple starting materials.