Reactivity of Rieke manganese: Synthesis of pyrrolidine and piperidine derivatives

Heterocycles

Volumn 49, Issue 1, 1998, Pages 85-88

  Hojo, Makoto ^a   Yoshizawa, Junji ^a   Funahashi, Yoshihiro ^a   Okada, Ryo ^a   Nakamura, Shin Ya ^a   Tateiwa, Jun Ichi ^a   Hosomi, Akira ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; CHLORIDE; KETONE; MANGANESE CHLORIDE; MANGANESE DERIVATIVE; NAPHTHALENE DERIVATIVE; PIPERIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 0032585383     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-98-s37     Document Type: Article

References (12)

1. A part of this study was presented in the 67th annual meeting of the Chemical Society of Japan, 1994, Tokyo, 2K1 36; abstract II-p.1092.
2. G. Cahiez, 'Encyclopedia of Reagents for Organic Synthesis,' ed. by L. Paquette, Wiley, Chichester, 1995, pp. 925-928.
3. For reviews, see P. Knochel, Synlett, 1995, 393;
4. P. Knochel and R. D. Singer, Chem. Rev., 1993, 93, 2117.
5. M. Hojo, H. Harada, H. Ito, and A. Hosomi, J. Am. Chem. Soc., 1997, 119, 5459;
6. M. Hojo, H. Harada, H. Ito, and A. Hosomi, Chem. Commun., 1997, 2077.
7. S. -H. Kim, M. V. Hanson, and R. D. Rieke, Tetrahedron Lett., 1996, 37, 2197.
8. Although the amounts of these byproducts actually produced in this stepwise acylation were not analyzed, the reduction of iodide (1) with Rieke manganese without the consecutive addition of propionyl chloride afforded 93% of N,N-dipropyltosylamide and 7% of N-allyl-N-propyltosylamide.
9. In a crude reaction mixture obtained by the reaction in ether, benzene (about 40%) and bromobenzene (about 10%) were detected by GC and GCMS.
10. K. Takai, T. Ueda, N. Ikeda, and T. Moriwake, J. Org. Chem., 1996, 61, 7990.
11. Based on pivalaldehyde (0.5 mmol), 74% of thioanisol (0.37 mmol), 52% of 1,2-bis(phenylthio)ethane (0.26 mmol) and 50 % of bis(phenylthio)methane (0.25 mmol) were produced as byproducts.
12. N-Allyltosylamide may be produced through β-elimination from an anionic intermediate.