Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 9, Pages 4261-4269Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo400073d
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Funding
- National Natural Science Foundation of China [21072127, 21032006, 21072216, 21172141]
- Science Foundation of Shanghai Municipal Commission of Sciences and Technology [10JC1405600]
- Ministry of Science and Technology of China [2010CB12610, 2011BAE06B05]
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Nucleophile-dependent regioselectivities in the nuclephilic reaction of (S)-4-benzyl-2-fluoroalkyl-1,3-oxazoline to different types of fluorinated compounds were investigated experimentally and theoretically. The ring opening of (S)-4-benzyl-2-bromodifluoromethyl-1,3-oxazoline by arenethiolates exclusively occurred at the C5 position of the 1,3-oxazoline ring, whereas completely different regioselectivity was observed for a unimolecular radical nucleophilic substitution (S(RN)1) at the terminal bromine atom of the CF2Br group when arenolates were employed as the nucleophiles. The reaction of (S)-4-benzyl-2-fluoromethyl-1,3-oxazoline with nucleophiles such as arenethiols, arenols, and TMSCl underwent nucleophilic ring opening in a regiospecific way, while the use of TMSCF3 was determined to proceed through nucleophilic addition to the C=N bond.
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