The chemistry of acylals. Part II. Formation of nitriles by treatment of acylals with trimethylsilyl azide in the presence of a lewis acid

Tetrahedron Letters

Volumn 39, Issue 35, 1998, Pages 6361-6364

  Sandberg, Marcel ^a,b   Sydnes, Leiv K ^b  

^a SINTEF   (Norway)

^b UNIVERSITY OF BERGEN   (Norway)

Author keywords

Acylals; Azides; Benzonitriles

Indexed keywords

ALDEHYDE; BENZONITRILE; NITRILE; TRIMETHYLSILYL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; SYNTHESIS;

EID: 0032572855     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01309-4     Document Type: Article

References (22)

1. [3] Kryshtal GV, Bogdanov VS, Yanovskaya LA, Volkov YP, Trusova EI. Izv. Akad. Nauk SSSR, Ser. Khim. 1981:2820-2823; Bull. Acad. Sci. USSR, Div. Chem. Sci. [Eng.] 1981;30:2351-2354.
2. [3] Kryshtal GV, Bogdanov VS, Yanovskaya LA, Volkov YP, Trusova EI. Izv. Akad. Nauk SSSR, Ser. Khim. 1981:2820-2823; Bull. Acad. Sci. USSR, Div. Chem. Sci. [Eng.] 1981;30:2351-2354.
3. [4] Kryshtal GV, Bogdanov VS, Yanovskaya LA, Volkov YP, Trusova EI. Tetrahedron Lett. 1982;23:3607-3610.
4. [5] Ghribi A, Alexakis A, Normant JF. Tetrahedron Lett. 1984;25:3079-3082.
5. [6] Trost BM, Vercauteren J. Tetrahedron Lett. 1985;26:131-134
6. [7] Trost BM, Lee CB, Weiss JM. J. Am. Chem. Soc. 1995;117:7247-7248.
7. [8] Part I in this series: Sydnes LK, Sandberg M. Tetrahedron 1997; 53:12679-12690.
8. [9] Part III in this series: Sydnes LK, Sandberg M. Manuscript in preparation.
9. [10] Hurd CD, Green FO. J. Am. Chem. Soc. 1941; 63: 2201-2204.
10. [11] Narayana C, Padmanabhan S, Kabalka GW. Tetrahedron Lett. 1990; 31: 6977-6978.
11. [12] Ku Y-Y, Patel R, Sawick D. Tetrahedron Lett. 1993; 34: 8037-8040.
12. [13] Michael A, Weiner N. J. Am. Chem. Soc. 1936; 58: 680-684.
13. [14] Grundmann C. Herstellung von Azidoverbindungen. In: Stroh R, editor. Methoden der Organischen Chemie (Houben-Weyl) - Stickstoffverbingungen I. Band X/3. Stuttgart: Georg Thieme, 1965:785-812.
14. [15] Reeves WP, Bahr ML. Synthesis 1976: 823.
15. [16] Marti MJ, Rico I, Ader JC, de Savignac A, Lattes A. Tetrahedron Lett. 1989; 30: 1245-1248.
16. [17] Priebe H. Acta Chem. Scand. B 1984; 38: 895-898.
17. [18] Murahashi S-I, Taniguchi Y, Imada Y, Tanigawa Y. J. Org. Chem. 1989; 54: 3292-3303.
18. [19] Nishiyama K, Oba M, Watanabe A. Tetrahedron 1987; 43: 693-700.
19. [20] Kirchmeyer S, Mertens A, Olah G. Synthesis 1983:500-502.
20. [21] Moriarty R, Hou K-C, Miller R. Synthesis 1984:683-685.
21. [22] Kyba EP. Alkyl Azides and Nitrenes. In: Scriven EFV, editor. Azides and Nitrenes - Reactivity and Utility. Orlando: Academic Press, 1984:1-34.
22. [23] Tennant G. General Methods for the Synthesis of Aliphatic, Alicyclic, and Aromatic Nitriles. In: Sutherland IO, editor. Comprehensive Organic Chemistry. Vol. 2. Oxford: Pergamon Press, 1979:528-539.