Straightforward Conversion of Alcohols into Nitriles

REFERENCES

• Rappoport , Z. The Chemistry of the Cyano Group ; Wiley Interscience : New York , 1970 .
   Google Scholar
• Kornblum , N. ; Smiley , R. A. ; Blackwood , R. K. ; Iffland , D. C. The mechanism of the reaction of silver nitrite with alkyl halides: The contrasting reactions of silver and alkali metal salts with alkyl halides: The alkylation of ambident anions . J. Am. Chem. Soc. 1955 , 77 , 6269 .
   Google Scholar
• (a) Brett , D. ; Downie , I. M. ; Lee , J. B. Sugars with potential antiviral activity: Conversion of hydroxy compounds to nitriles . J. Org. Chem. 1967 , 32 , 855 ; (b) Loibner , H. ; Zbiral , E. Reaktionen mit phosphororganischen verbindungen, XLI: Neuartige synthetische aspekte des systems triphenylphosphin-azodicarbonsäureester-hydroxyverbindung . Helv. Chim. Acta 1976 , 59 , 2100 ; (c) Mizuno , A. ; Hamada , Y. ; Shioiri , T. New methods and reagents in organic synthesis, 6: A simple one-pot conversion of primary alcohols to nitriles having one C-atom more . Synthesis 1980 , 1007 ; (d) Davis , R. ; Untch , K. G. Direct one-step conversion of alcohols into nitriles . J. Org. Chem. 1981 , 46 , 2985 ; (e) Wilk , B. K. A convenient preparation of alkyl nitriles by the Mitsunobu procedure . Synth. Commun. 1993 , 23 , 2481 ; (f) Aesa , M. C. ; Baan , G. ; Novak , L. ; Szantay , C. Preparation of unsaturated nitriles by the modification of Mitsunobu–Wilk procedure II: Carbon elongation of β-acetylenic alcohols . Synth. Commun. 1995 , 25 , 2575 ; (g) Tsunoda , T. ; Uemoto , K. ; Nagino , C. ; Kawamura , M. ; Kaku , H. ; Ito , S. A facile one-pot cyanation of primary and secondary alcohols: Application of some new Mitsunobu reagents . Tetrahedron Lett. 1999 , 40 , 7355 .
   PubMed Web of Science ®Google Scholar
• Iranpoor , N. ; Firouzabadi , H. ; Akhalaghinia , B. ; Nowrouzi , N. Conversion of alcohols, thiols, and trimethysilyl ethers to alkyl cyanides using triphenylphosphine/2,3-dichloro-5,6-dicyanobenzoquinone/n-Bu4NCN . J. Org Chem. 2004 , 69 , 2562 .
   PubMed Web of Science ®Google Scholar
• Masutani , K. ; Minowa , T. ; Hagiwara , Y. ; Mukaiyama , T. Cyanation of alcohols with diethyl cyanophosphonate and 2,6-dimethyl-1,4-benzoquinone by a new type of oxidation–reduction condensation . Bull. Chem. Soc. Jpn. 2006 , 79 , 1106 .
   Google Scholar
• Godfrey , S. M. ; McAuliffe , C. A. ; Pritchard , R. G. ; Sheffield , J. M. The synthesis and characterisation of R3PXCN [R = 2,4,6-(CH3O)3C6H2, 2,6-(CH3O)2C6H3, NCCH2CH2, C6H11 or PhCH2; X˭Br or I] in the solid state and in solution . J. Chem. Soc., Dalton Trans. 1998 , 1919 .
   Google Scholar