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0242432419
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II salen also catalyzed the formation of propylene carbonate in the presence of Lewis bases, see:
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II salen also catalyzed the formation of propylene carbonate in the presence of Lewis bases, see: Shen Y.-M., Duan W.-L., Shi M. J. Org. Chem. 68:2003;1559-1562.
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1242266790
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III TPP (Cl) complex was synthesized according to a known literature procedure, see:
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III TPP (Cl) complex was synthesized according to a known literature procedure, see: Tseet al. Organometallics. 17:1998;2651-2655.
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Tse1
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85030913166
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note
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2 for 5 min to allow the system to equilibrate and then heated to 120°C for the allotted time. The vessel was then cooled to ambient temperature by placement in a dry ice/water bath. The pressure was then released and the contents transferred to a 50 mL round-bottom flask. Unreacted substrate and solvent were removed in vacuo and the product was then isolated via Kugelrohr distillation (65°C/0.2 mmHg). Analysis of the product was carried out via GC-MS, GC (using an instrument equipped with FID detector and a 30 m HP-5 capillary column with 0.32 mm inner diameter and 0.25 mm film thickness. Temperature program: initial time=0, initial temperature=50°C, rate=15°C/min; final time=10 min, final temperature=250°C), and NMR.
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22
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85030911267
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note
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No reaction was observed in the absence of Lewis base.
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24
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85030912123
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note
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4Cl does not lead to a significant increase in TOF, suggesting that the more Lewis basic DMAP is primarily responsible for the ring-opening of the Co-activated epoxide.
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25
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85030907366
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note
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That the ring opening of the epoxide occurs at the least substituted position, as consistent with a nucleophilic ring-opening mechanism, should not change the stereochemistry at the more substituted carbon of the epoxide. This is indeed the case: the reaction of chirally pure (S)-(+)propylene oxide results in pure (S)-(+) propylene carbonate.
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27
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85030903324
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2 adduct has been isolated and characterized, see:
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2 adduct has been isolated and characterized, see: Francoet al. Tetrahedron Lett. 43:2002;4091-4093.
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(2002)
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, vol.43
, pp. 4091-4093
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Franco1
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85030905492
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note
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Cyclohexene oxide was employed as substrate and found to yield only the corresponding polycarbonate.
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31
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85030914131
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note
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+): 178.0624. Found: 178.0623.
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