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Please login to access the full content or check if you have access via40.4.2.1.5.3 Variation 3: From Azacyclanes Using N-Chlorosuccinimide
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Wille, U., Science of Synthesis, (2009) 40, 918.
N-Chloropyrrolidines 70 (n = 1) and piperidines 70 (n = 2) can be synthesized from the parent heterocycles, or their hydrochlorides, by treating them with N-chlorosuccinimide using either a vacuum gas/solid chlorination technique,[24,133] or as solutions in tetrahydrofuran,[204] diethyl ether[89,134,200] or dichloromethane.[201,205] Enantiomerically pure (R)-(–)-1-chloro-2-methylpyrrolidine (71) is obtained from (R)-2-methylpyrrolidine using N-chlorosuccinimide in diethyl ether.[193] Similar conditions can be applied to the N-chlorination of 2,3-dihydro-1H-benzo[de]isoquinoline (72) (Scheme 42).[206]
Meeeee 88 Meeeeeeee ee M-Meeeeeeeeee Meeeeeeeeeee Meeee M-Meeeeeeeeeeeeeeee[888,888,888]
Meeeeeeeeeee Meeeeeeee
(M)-(–)-8-Meeeee-8-eeeeeeeeeeeeeeeee (88):[888]
MMMMMMM: M-Meeeeeeeeeee eee eeee eeeeeeee eeeeeee eee eeeeee eeeeee ee eeeeeee eeeeee e eeeeee eeeeee.
M eeee ee (M)-(–)-8-eeeeeeeeeeeeeeeee (8.88 e, 8.88 eeee) ee eee Me8M (8 eM) eee eeeeee eeeee eeee eeeeeeee ee e eeeeeeeeee ee MMM (8.8 e, 88.8 eeee) ee eee Me8M (88 eM), eee eee eeeeeee eee eeeeeee eee 8 e. Mee eeeeeeeeeee eee eeeeeeee eee eee eee eeeeeee eee eeeeeee. Meeeeeeeeeee (eeee eeeeeeeeeee ee ee 88°M) ee eee eeeeeee eeee eee eeeee eeeeeeee; eeeee: 8.88 e (88%); ee 88–88°M/88 Meee; [α]M88 −88.8 (e 8.88, MeMM).
References
[24] | Meee, M.; Meeeee, M., Meee. Mee., (8888) 888, 8888. |
[89] | Meeeeeee, M. M.; Meeeeee, M. M. M.; Meeeeee, M. M.; Meeee, M. M. M. M., Meeeeeeeee. Meeeee., (8888) 8, 888. |
[133] | Meeeeeeee, M.-M.; Meeee, M. M., Meeeeeeee, (8888), 8888. |
[134] | Me, M. M.; Meeee, M. M., Meeeeeeeeee, (8888) 88, 88888. |
[193] | Meeeeeeeeeee, M. M.; Meeee, M. M.; Meeeee, M. M.; Meeeeeeee, M. M., Meeeeeeeeee, (8888) 88, 88. |
[200] | Meeeee, M.; Meeeeee, M.; Meeeeee, M. M., Meeeeeeeeee, (8888) 88, 888. |
[201] | Meeeee, M. M.; Meeeeee, M. M.; Meeeee, M. M.; Meeeeee, M. M., Meeeeeeeeee, (8888) 88, 8888. |
[204] | Meeee, M. M.; Meeeeee, M. M. M.; Meeeeee, M. M.; Meeeeee, M.; Meeeeeee, M., Mee. Meee., (8888) 8, 888. |
[205] | Meeeeeee, M.; Meeeeeeeeeeee, M.; Meeeeee, M., Meee. Mee., (8888) 888, 8888. |
[206] | Meeee, M.; Mee, M.; Meee, M. M.; Meeee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) M 88e8, 888.