Regioselective Amidation of Allylic α-Hydroxyphosphonates with Nitriles: A Convenient Route to (3-Acetylamino-1-alkenyl)-phosphonates

Monatshefte fur Chemie

Volumn 127, Issue 2, 1996, Pages 177-183

  Ohler E ^a   Kanzler, S ^a  

^a INSTITUT FÜR ORGANISCHE CHEMIE   (Austria)

Author keywords

1,3 Transposition; Dialkyl (1 hydroxy 2 alkenyl)phosphonates; Dialkyl (3 acetylamino 1 alkenyl)phosphonates; Ritter reaction

Indexed keywords

EID: 1842529921     PISSN: 00269247     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF00807399     Document Type: Article

References (23)

1. Öhler E, Zbiral E (1991)Chem Ber 124: 175
2. Öhler E, Zbiral E (1991) Synthesis: 357
3. Blackburn GM, Kent DE (1986) J Chem Soc Perkin Trans 1:913 Blackburn GM, Kent DE (1981) J Chem Soc Chem Commun:511
4. Blackburn GM, Kent DE (1986) J Chem Soc Perkin Trans 1:913 Blackburn GM, Kent DE (1981) J Chem Soc Chem Commun:511
5. Belykh OA, Dogadina AV, Ionin BI, Petrov AA (1985) Zh Obshch Khim 55: 1870, Engl Transl (1985): 1662 Cabioch JL, Denis JM (1989) J Organomet Chem 377: 227
6. Belykh OA, Dogadina AV, Ionin BI, Petrov AA (1985) Zh Obshch Khim 55: 1870, Engl Transl (1985): 1662 Cabioch JL, Denis JM (1989) J Organomet Chem 377: 227
7. Cooper D, Trippett S (1981) J Chem Soc Perkin Trans 1: 2127
8. Lu X, Tao X, Zhu J, Sun X, Xu J (1989) Synthesis: 848
9. Zhu J, Lu X (1987) Tetrahedron Lett: 1897
10. Öhler E, Kotzinger S (1993) Liebigs Ann Chem: 269 Öhler E, Kanzler S (1994) Liebigs Ann Chem: 867
11. Öhler E, Kotzinger S (1993) Liebigs Ann Chem: 269 Öhler E, Kanzler S (1994) Liebigs Ann Chem: 867
12. Öhler E, Kotzinger S (1993) Synthesis: 497
13. Zhu J, Lu X (1987) J Chem Soc Chem Commun: 1318 Lu X, Sun J, Zhu J (1992) Heteroatom Chem 3: 551
14. Zhu J, Lu X (1987) J Chem Soc Chem Commun: 1318 Lu X, Sun J, Zhu J (1992) Heteroatom Chem 3: 551
15. Öhler E, Kanzler S (1995) Synthesis: 539 Öhler E, Kanzler S (1996) Phosphorus, Sulfur, Silicon (in press)
16. Öhler E, Kanzler S (1995) Synthesis: 539 Öhler E, Kanzler S (1996) Phosphorus, Sulfur, Silicon (in press)
17. For leading references see Ref. [9]
18. Krimen LI, Cota DJ (1969) Org React 17: 213 Bishop R (1991) Ritter-type reactions. In: Trost BM, Fleming I, Winterfeldt E (eds) Comprehensive organic synthesis, vol 6. Pergamon Press, p 261
19. Krimen LI, Cota DJ (1969) Org React 17: 213 Bishop R (1991) Ritter-type reactions. In: Trost BM, Fleming I, Winterfeldt E (eds) Comprehensive organic synthesis, vol 6. Pergamon Press, p 261
20. For recent examples of Ritter-type reactions with concomitant allylic rearrangement see: Kaboré IZ, Khuong-Huu Q, Pancrazi A (1978) Tetrahedron 34: 2815; Nayyar NK, Reddy MM, Iqbal J (1991) Tetrahedron Lett 47: 6965; Mukhopadhyay M, Reddy MM, Maikap GC, Iqbal J (1995) J Org Chem 60: 2670
21. For recent examples of Ritter-type reactions with concomitant allylic rearrangement see: Kaboré IZ, Khuong-Huu Q, Pancrazi A (1978) Tetrahedron 34: 2815; Nayyar NK, Reddy MM, Iqbal J (1991) Tetrahedron Lett 47: 6965; Mukhopadhyay M, Reddy MM, Maikap GC, Iqbal J (1995) J Org Chem 60: 2670
22. For recent examples of Ritter-type reactions with concomitant allylic rearrangement see: Kaboré IZ, Khuong-Huu Q, Pancrazi A (1978) Tetrahedron 34: 2815; Nayyar NK, Reddy MM, Iqbal J (1991) Tetrahedron Lett 47: 6965; Mukhopadhyay M, Reddy MM, Maikap GC, Iqbal J (1995) J Org Chem 60: 2670
23. Texier-Boullet F, Foucaud A (1982) Synthesis: 165