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Beilstein J. Org. Chem. 2007, 3, No. 47, doi:10.1186/1860-5397-3-47
Graphical Abstract
Scheme 1: Reactivity of 2-oxoalkylxanthates toward 1-decene in the presence of Et3B/O2: competition between a...
Figure 1: Starting xanthates and olefins.
Figure 2: Adducts between xanthates and olefins.
Scheme 2: Postulated mechanism for the reaction of 2-oxoalkyl xanthates with olefins in the presence of Et3B.
Beilstein J. Org. Chem. 2007, 3, No. 46, doi:10.1186/1860-5397-3-46
Figure 1: Xanthates 1a, 2a and their corresponding alkanes.
Figure 2: Deuterated O-ethyl-S-ethyl dithiocarbonates 3–5, deuterated adduct 1d and alkane 1e.
Figure 3: Kinetics of the reduction of compound 1a in C6H6 at 20°C.
Scheme 1: Preparation of Et3B-d15.
Beilstein J. Org. Chem. 2007, 3, No. 45, doi:10.1186/1860-5397-3-45
Figure 1: Reaction of α-acylxanthate 1a with 1-decene and Et3B/air.
Figure 2: Xanthates and thionoimidazolides 2–16 and their reduced derivatives.
Scheme 1: Reduction of xanthate 17a at different temperatures with Et3B (5 equiv.)/air.
Scheme 2: Reduction of S-alkylxanthates and O-alkylxanthates.
Scheme 3: Reduction of O-alkyl-S-methyl xanthate 19, thionoimidazolide 21 and iodide 22 by Et3B/air at 20°C.
Scheme 4: Products formed through a putative 1,5-hydrogen atom transfer.