Surface-Mediated Hydrohalogenation of Isoprene: A Facile Preparation of Prenyl Halides

References

• Simas , A.B.C. , da Silva , A.J.M. , Coelho , A.L. and Costa , P.R.R. 2001 . Regioselective lithiation of a pterocarpan skeleton: the first synthesis of (+/−)-4′-dehydroxycabenegrin A-I . Tetrahedron Lett. , 42 ( 25 ) : 4111 – 4113 .
   Google Scholar
• Morales-Rios , M.S. , Suárez-Castillo , O.R. , Trujillo-Serrato , J.J. and Joseph-Nathan , P. 2001 . Total synthesis of five indole alkaloids from marine bryozoan Flustra foliacea . J. Org. Chem. , 66 ( 4 ) : 1186 – 1192 .
   PubMedGoogle Scholar
• Crimmins , M.T. , Emmitte , K.A. and Katz , J.D. 2000 . Diastereoselective alkylations of oxazolidinone glycolates: a useful extension of the evans asymmetric alkylation . Org. Lett. , 2 ( 14 ) : 2165 – 2167 .
   PubMedGoogle Scholar
• Kanai , T. , Irifune , S. , Ishii , Y. and Ogawa , M. 1989 . One-pot synthesis of homoallylic alcohols via a facile conversion of allylic alcohols, into allylic iodides . Synthesis , : 283 – 286 .
   Google Scholar
• Magid , R.M. , Fruchey , O.S. , Johnson , W.L. and Allen , T.G. 1979 . Hexachloroacetone-triphenylphosphine-mild reagent for the regioselective and stereospecific production of allylic chlorides from the alcohols . J. Org. Chem. , 44 ( 3 ) : 359 – 363 .
   Google Scholar
• Barbot , F. and Miginiac , P. 1977 . Action of Me2C=CHCH2M (M=MgX, ZnBr, Li) prenylic type organometal derivatives with diisopropylketone—reversibility of reaction . Bull. Soc. Chim. Fr. , : 113 – 116 .
   Google Scholar
• Crombie , L. , Harper , S.H. and Sleep , K.C. 1957 . Experiments on the synthesis of the pyrethrins. Part XIII. Total synthesis of (+/−)-cis- and -trans-chrysanthemumdicarboxylic acid, (+/−)-cis- and -trans-pyrethric acid, and rethrins II . J. Chem. Soc. , : 2743 – 2754 .
   Google Scholar
• Staudinger , H. , Kreis , W. and Schilt , W. 1922 . Über die addition von halogenwasserstoff an isopren . Hel. Chim. Acta , 5 ( 2 ) : 743 – 756 .
   Google Scholar
• Prenyl chloride: US$ 23.70/5 g or US$ 80.40/25 g; prenyl bromide: US$ 12.00/1 g or US$ 25.20/10 g (Aldrich Handbook of Fine Chemicals, 2000–2001)
   Google Scholar
• Clark , J.H. and Macquarrie , D.J. 1996 . Environmentally friendly catalytic methods . Chem. Soc. Rev. , 25 ( 5 ) : 303 – 310 .
   Google Scholar
• Kropp , P.J. , Daus , K.A. , Tubergen , M.W. , Kepler , K.D. , Wilson , V.P. , Craig , S.L. , Baillargeon , M.M. and Breton , G.W. 1993 . Surface-mediated reactions. 3. Hydrohalogenation of alkenes . J. Am. Chem. Soc. , 115 ( 8 ) : 3071 – 3079 .
   Google Scholar
• de Mattos , M.C.S. and Sanseverino , A.M. 2000 . A convenient and simplified preparation of both enantiomers of α-terpinyl chloride . Synth. Commun. , 30 ( 11 ) : 1975 – 1983 .
   Web of Science ®Google Scholar
• Sanseverino , A.M. , de Mattos , M.C.S. and Kover , W.B. 2000 . Surface-mediated chemospecific hydrobromination of limonene: stereoselective transformation of the enantiomers of limonene into α-terpinyl bromide . J. Chem. Res. , : 346 – 347 .
   Google Scholar
• Sanseverino , A.M. and de Mattos , M.C.S. 2001 . Hydrobromination of alkenes with PBr3/SiO2: a simple and efficient regiospecific preparation of alkyl bromides . J. Braz. Chem. Soc. , 12 ( 5 ) : 685 – 687 .
   Google Scholar
• Lide , D.R. , ed. 1997–1998 . Handbook of Chemistry and Physics, , 78th Ed. Boca Raton : CRC Press .
   Google Scholar
• Späth , E. and Spitzy , W. 1925 . Synthesis of galegine . Chem. Ber. , 58B : 2273 – 2279 .
   Google Scholar
• Pouchert , C.P. and Behnke , J. 1993 . The Aldrich Library of ¹³ C and ¹ H FT NMR Spectra Vol. 1 , 139 Aldrich Chemical Co . Prenyl chloride: Ref.[5] Prenyl bromide: Prenyl Iodide: Ref.[4]
   Google Scholar
• Miller , J.A. , Scrimgeour , C.M. , Black , R. , Larkin , J. , Nonhebel , D.C. and Wood , H.C.S. 1973 . Formation of 1,1-dimethylallyl derivatives by reaction of 3,3-dimethylallyl halides with copper(II) chelates of acetylacetone and methyl acetoacetate . J. Chem. Soc. Perkin Trans. 1 , : 603 – 606 .
   Google Scholar
• Furniss , B.S. , Hannaford , A.J. , Smith , P.W.G. and Tatchell , A.R. 1996 . Vogel's Textbook of Practical Organic Chemistry, , 5th Ed. 437 – 438 . Singapore : Longman . 576–578
   Google Scholar
• Germann , F.E.E. and Traxler , R.N. 1927 . Preparation and melting points of pure di- and tri-iodide of phosphorus . J. Am. Chem. Soc. , 49 ( 2 ) : 307 – 312 .
   Google Scholar
• Lasne , M.-C. , Cairon , P. and Villemin , D. 1990 . Rapid synthesis of α,β unsaturated iodides: iodination under vacuum with solid diphosphorous tetraiodide . Synth. Commun. , 20 ( 1 ) : 41 – 44 .
   Web of Science ®Google Scholar