TY - JOUR
T1 - A Route to 5,5-Dithiospiroketals and to Long-Chain Monomers from the Biomass
AU - Dorokhov, Valentin S.
AU - Quiclet-Sire, Beátrice
AU - Zard, Samir Z.
N1 - Publisher Copyright:
© 2022 American Chemical Society. All rights reserved.
PY - 2022/4/22
Y1 - 2022/4/22
N2 - 5,5-Dithiospiroketals are prepared by a double radical addition of α,α′-bisxanthyl acetone to an alkene followed by ionic or thermal cleavage of the xanthate groups and acid-catalyzed ring closure. A modification employs α-chloro-α′-xanthyl acetone to give unsymmetrical derivatives. Reductive removal of the sulfur atoms with Raney nickel furnishes long-chain α,ω-diacids, diols, and diamines. Using biosourced alkenes, monomers and polymers can be obtained where essentially all the carbons are derived from the biomass.
AB - 5,5-Dithiospiroketals are prepared by a double radical addition of α,α′-bisxanthyl acetone to an alkene followed by ionic or thermal cleavage of the xanthate groups and acid-catalyzed ring closure. A modification employs α-chloro-α′-xanthyl acetone to give unsymmetrical derivatives. Reductive removal of the sulfur atoms with Raney nickel furnishes long-chain α,ω-diacids, diols, and diamines. Using biosourced alkenes, monomers and polymers can be obtained where essentially all the carbons are derived from the biomass.
U2 - 10.1021/acs.orglett.2c00855
DO - 10.1021/acs.orglett.2c00855
M3 - Article
C2 - 35404064
AN - SCOPUS:85128797106
SN - 1523-7060
VL - 24
SP - 2878
EP - 2882
JO - Organic Letters
JF - Organic Letters
IS - 15
ER -