Synthesis and Reactions of Vinylene Carbonate

Swern Oxidation of Bicyclo[2.2.1]hept-5-ene-2,3-diol and Its Pyrazine-fused Derivatives: An Improved Synthesis of Bicyclo[2.2.1]hept-5-ene-2,3-dione and An Unexpected Ring-Opening Reaction

“…Thus, we report here an improved synthesis of 1 starting from more readily available vinylene carbonate (4) [4]. Bicyclo[2.2.1]hept-5-ene-2,3-diol (6) was prepared by the Diels-Alder reaction of vinylene carbonate (4) and cyclopentadiene followed by the hydrolysis as described in the literature [5]. The total yield for the two steps was 78%.…”

Diels–Alder reaction of vinylene carbonate and 2,5-dimethylfuran: kinetic vs. thermodynamic control

“…The formation of such a compound was already mentioned in the first studies of Diels-Alder reactions with vinylene carbonate. 12 It is isolated as a single diastereomer, but its structure was not fully elucidated. A strong nuclear Overhauser effect (nOe) between the protons located at the ring junctions implies that they are all in an axial position.…”

A study on the intramolecular catalytic aldol cyclodehydration of 3,4-disubstituted 1,6-dialdehydes

“…To a solution of 14 [23,24] (114 mg, 1 mmol) in CH 2 Cl 2 (20 ml), Et 3 N (0.35 ml, 2.5 mmol) and then (COCl) 2 …”

“…To a solution of 14 [23,24] (570 mg, 5 mmol) in dry toluene (10 ml), pyridine (1.0 ml, 7.5 mmol) and phosgene (2.5 ml, 5 mmol) in a form of 20% solution in toluene, were added under argon atmosphere. After 2 h stirring at room temperature the solution was washed with brine, with 5% aq.…”