David M. Pearson et al.
FULL PAPERS
(CDCl3): d= 4.06 (s, 2H), 1.11 (s, 6H); anal. calcd. for
C5H8O3: C 51.72, H 6.94; found: C 51.48, H 6.91.
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4-Phenyl-1,3-dioxolan-2-one (2g): Purified by column
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chromatography (SiO2, 10% EtOAc/hexanes). 1H NMR
(CDCl3): d= 7.44ACHTUNGTRENNUNG(m, 3H), 7.36 (m, 2H), 5.68 (t, J=8.0 Hz,
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1H), 4.80 (dd, J=8.2, 8.6 Hz, 1H), 4.35 (dd, J=7.9, 8.6 Hz,
1H); anal. calcd. for C9H8O3: C 65.85, H 4.91; found: C
65.58, H 4.83.
4-(Hydroxymethyl)-1,3-dioxolan-2-one (2h): Purified by
column chromatography (SiO2, 6:1 CHCl3/acetone).
1H NMR (CD3CN): d=4.74 (m, 1H), 4.46 (dt, J=0.9,
8.4 Hz, 1H), 4.29 (ddd, J=0.9, 6.0, 8.4 Hz, 1H), 3.77 (dq,
J=2.8, 4.7, 12.7 Hz, 1H), 3.57 (dq, J=3.7, 5.4, 12.7 Hz, 1H),
3.26 (t, J=5.7 Hz, 1H); anal. calcd. for C4H6O4: C 40.68, H
5.12; found: C 40.68, H 4.91.
4-Vinyl-1,3-dioxolan-2-one (2i): Purified by column chro-
matography (SiO2, 40% EtOAc/hexanes). 1H NMR
(CDCl3): d=5.90 (ddd, J=6.9, 10.5, 17.2 Hz, 1H), 5.51 (d,
J=17.2 Hz, 1H), 5.45 (d, J=10.5 Hz, 1H), 5.12 (q, J=
7.6 Hz, 1H), 4.60 (dd, J=8.3, 8.6 Hz, 1H), 4.16 (dd, J=7.6,
8.6 Hz, 1H); anal. calcd. for C5H6O3: C 52.63, H 5.30;
found: C 52.37, H 5.27.
1,3-Dioxan-2-one (2k): Purified by column chromatogra-
1
phy (SiO2, 6:1 CHCl3/acetone). H NMR (CDCl3): d=4.44
(t, J=5.6 Hz, 4H), 2.14 (p, J=5.6 Hz, 2H); anal. calcd. for
C4H6O3: C 47.06, H 5.92; found: C 46.79, H 5.84
5,5-Dimethyl-1,3-dioxan-2-one (2l): Purified by column
chromatography (SiO2, 5% acetone/CHCl3). 1H NMR
(CDCl3): d=4.14 (s, 4H), 1.51 (s, 6H); anal. calcd. for
C6H10O3: C 55.37, H 7.74; found: C 55.66, H 7.86.
5,5-Dimethoxy-1,3-dioxan-2-one (2m): Purified by column
chromatography (SiO2, 10% acetone/CHCl3). 1H NMR
(CDCl3): d=4.29 (s, 3H), 3.33 (s, 6H); anal. calcd. for
C6H10O5: C 44.45, H 6.22; found: C 44.41, H 6.18.
Benzyl 5-methyl-2-oxo-1,3-dioxane-5- carboxylate (2n):
Purified by column chromatography (SiO2, 5% CHCl3/ace-
1
tone). H NMR (CDCl3): d=7.36 (m, 5H), 5.22 (s, 2H), 4.71
(d, J=10.8 Hz, 2H), 4.20 (d, J=10.8 Hz, 2H), 1.34 (s, 3H);
anal. calcd. for C13H14O5: C 62.39, H 5.64; found: C 62.12, H
5.74.
Acknowledgements
This research was supported by The Global Climate and
Energy Project at Stanford University and the DOE (DE-
FG02-10ER16198). D. M. P. would like to thank the Burt
and Deedee McMurtry Stanford Graduate Fellowship for fi-
nancial support.
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