"Syn-effect" in nucleophilic addition of amines to 1,3-dienylsulfone

Chemistry Letters

Volumn 35, Issue 5, 2006, Pages 514-515

  Yamazaki, Masao ^a   Guha, Samar Kumar ^a   Ukaji, Yutaka ^a   Inomata, Katsuhiko ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

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Indexed keywords

EID: 33746590747     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2006.514     Document Type: Article

References (12)

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2. The "syn-effect" is herein defined as an effect which stabilizes the syn-conformation against the steric hindrance at the transition state.
3. Related studies on the "syn-effect" : a) A. Shibayama, T. Nakamura, T. Asada, T. Shintani, Y. Ukaji, H. Kinoshita, K. Inomata, Bull. Chem. Soc. Jpn. 1997, 70, 381.
4. b) T. Nakamura, S. K. Guha, Y. Ohta, D. Abe, Y. Ukaji, K. Inomata, Bull. Chem. Soc. Jpn. 2002, 75, 2031.
5. c) S. K. Guha, A. Shibayama, D. Abe, Y. Ukaji, K. Inomata, Chem. Lett. 2003, 32, 778.
6. d) S. K. Guha, Y. Ukaji, K. Inomata, Chem. Lett. 2003, 32, 1158.
7. e) S. K. Guha, A. Shibayama, D. Abe, M. Sakaguchi, Y. Ukaji, K. Inomata, Bull. Chem. Soc. Jpn. 2004, 77, 2147.
8. f) H. Takenaka, Y. Ukaji, K. Inomata, Chem. Lett. 2005, 34, 256.
9. g) N. Takeda, T. Chayama, H. Takenaka, Y. Ukaji, K. Inomata, Chem. Lett. 2005, 34, 1140.
10. F. Näf, R. Decorzant, S. D. Escher, Tetrahedron Lett. 1982, 23, 5043.
11. Radical mechanism could be ruled out because the presence of TEMPO, N-hydroxyphthalimide, galvinoxyl free radical did not affect the Z/E ratios.
12. The effective n → π* interaction cannot be involved in the conformation F.