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Communication | Special issue | Vol 49, No. 1, 1998, pp.85-88
Published online, 1st January, 1970
DOI: 10.3987/COM-98-S37
Reactivity of Rieke Manganese: Synthesis of Pyrrolidine and Piperidine Derivatives

Makoto Hojo, Junji Yoshizawa, Yoshihiro Funahashi, Ryo Okada, Shin-ya Nakamura, Jun-ichi Tateiwa, and Akira Hosomi*

*Department of Chemistry, University of Tsukuba, Tsukuba, Ibaraki, 305-8571, Japan


Low-valent manganese generated by the reduction of manganese(II) chloride using lithium naphthalenide (Rieke manganese) promotes reactions of alkyl halides with electrophiles such as acyl chloride, aldehyde, and ketone to afford alkylation products. N-Haloalkyl-N-allyltosylamides are converted to pyrrolidine and piperidine derivatives in high yields. In the reactions of aromatic aldehyde and ketone, pinacol-type coupling products are produced.