Sample reactions
intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 90 min, 85%
intermediate structure
intermediate structure
DMSO, i-Pr2NEt, (CF3CO)2O
CH2Cl2
-60 to 0 °C, , 85% (2 steps)
intermediate structure
intermediate structure
DMSO, i-Pr2NEt, (CF3CO)2O
CH2Cl2
-60 to 0 °C, , 76% (2 steps)
intermediate structure
intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 6 d, 91% (2 steps)
intermediate structure
intermediate structure
Phosgene, DMSO, Et3N
CH2Cl2
-78 °C to RT, 30 min, 83% (2 steps)
intermediate structure
intermediate structure
(COCl)2, DMSO, i-Pr2NEt
CH2Cl2
intermediate structure
intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 to 0 °C, 90 min, 92% (3 steps)
intermediate structure
intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 35 min
intermediate structure
intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 30 min, 95%
intermediate structure
intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 10 h
intermediate structure
intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 to 0 °C, ON, 92%
intermediate structure
intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 75 min, 97%
intermediate structure
intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 75 min, 94% (2 steps)
intermediate structure
intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 45 min, 97%
intermediate structure
intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 75 min, 95%
intermediate structure
intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C, 70 min, 98%
intermediate structure
intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C, , 96%
intermediate structure
intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
-70 °C to RT, 40 min, 99%
intermediate structure
intermediate structure
DBU, DMSO, (CF3CO)2O
CH2Cl2
-78 °C to RT, 21 h
intermediate structure
intermediate structure
DMSO, Et3N, (CF3CO)2O
CH2Cl2
-78 °C to RT, 50 min, 57-68% (3 steps)
intermediate structure
intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 2.5 h, 93%
intermediate structure
intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C
intermediate structure
intermediate structure
(COCl)2, Et3N
DMSO
-78 °C to RT, 2.5 h, 83%
intermediate structure
intermediate structure
(COCl)2, DMSO, i-Pr2NEt
CH2Cl2
-78 °C to RT, 40 min
intermediate structure
intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 5.5 h, 100%
intermediate structure
intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 2 h
intermediate structure
intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 2 h
intermediate structure
intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C
intermediate structure
intermediate structure intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 22 min, 62% (2 steps)
"Also isolated was the C4-ketone (10 % yield)."
intermediate structure
intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 to 0 °C, 105 min, 91%
intermediate structure
intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 2 h, 98%
intermediate structure
intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 85 min, 87%
intermediate structure
intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
intermediate structure
intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 to 0 °C, 90 min
intermediate structure
intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C, , 91%
intermediate structure
intermediate structure
(COCl)2, DMSO, Et3N, Ph3P=CHCO2Et
CH2Cl2
-65 °C to RT, 5 h
intermediate structure
intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
intermediate structure
intermediate structure
(COCl)2, DMSO, Et3N
THF
-78 °C to RT, 23 min, 93%
intermediate structure
intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
-60 °C to RT, 50 min, 80%
intermediate structure
intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT
intermediate structure
intermediate structure
DMSO, Et3N, (CF3CO)2O
CH2Cl2
-78 °C to RT, 100 mnin, 85%
intermediate structure
intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C to RT, 80 min
intermediate structure
intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 to 0 °C, 2.5 h, 98%
intermediate structure
intermediate structure
(COCl)2, DMSO, Et3N
CH2Cl2
-78 °C, 80 min, 100%
intermediate structure