Catalysis of the Reaction of Cholesteryl Acetate with 4‐Phenyl‐1,2,4‐triazoline‐3,5‐dione by Lithium Perchlorate

References

• Deshmukh , M. B. , Suryawanshi , A. W. , Mali , A. R. and Dhongade Desai , S. R. 2004 . New route to synthesis and QSAR study of 1,2,4‐aryl substituted triazoles . Synth. Commun. , 34 ( 14 ) : 2655 – 2658 . See for example, and references therein
   Web of Science ®Google Scholar
• Beuchet , P. , El kihel , L. , Dherbomez , M. , Charles , G. and Letourneux , Y. 1998 . Synthesis of 6(α,β) aminocholestanols as ergosterol biosynthesis inhibitors . Bioorg. Med. Chem. Lett. , 8 : 3627 – 3630 . and references therein
   Google Scholar
• Davies , A. G. and Kinart , W. J. 1993 . Catalysis of ene reactions by lithium perchlorate . J. Chem. Soc., Perkin Trans. , 2 : 2281 – 2284 .
   Google Scholar
• Kinart , W. J. 1994 . Catalysis of ene reactions by lithium perchlorate . J. Chem. Res. Synop. , : 486 – 487 .
   Google Scholar
• Kinart , W. J. , Tylak , I. and Kinart , C. M. 1999 . Insertion of N˭N and O˭O bonds in tin and lead allyl bonds in metalloene reactions catalysed by lithium perchlorate . J. Chem. Res. Synop. , : 46 – 47 .
   Google Scholar
• Kinart , W. J. , Śnieć , E. , Tylak , I. and Kinart , C. M. 2000 . Studies on the catalysis of ene reactions by lithium perchlorate in different solvents . Phys. Chem. Liq. , 38 : 193 – 201 .
   Web of Science ®Google Scholar
• Kinart , W. J. , Kinart , C. M. and Tylak , I. 2000 . Solvent and salt effects on the reactions of allyltin (IV) compounds with singlet oxygen, 4‐phenyl‐1,2,4‐triazoline‐3,5‐dione and diethyl azodicarboxylate with different olefins by lithium perchlorate . J. Organomet. Chem. , 608 : 49 – 53 .
   Web of Science ®Google Scholar
• Kinart , W. J. , Kinart , C. M. , Tylak , I. and Mikołajczak , K. 2001 . Studies on the catalysis of ene reactions of 4‐phenyl‐1,2,4‐triazoline‐3,5‐dione and diethyl azodicarboxylate with different olefins by lithium perchlorate . Phys. Chem. Liq. , 40 : 405 – 410 .
   Google Scholar
• Cheng , C.‐C. , Seymour , C. A. , Petti , M. A. , Greene , F. D. and Blount , J. F. 1984 . Reaction of electrophiles with unsaturated systems: Triazolinedione‐olefin reactions . J. Org. Chem. , 49 : 2910 – 2916 .
   Web of Science ®Google Scholar
• Dang , H.‐S. and Davies , A. G. 1991 . Stereoselectivity in the ene reaction of syn‐ and anti‐1‐(4‐tert‐butylcyclohexylidene)‐4‐tert‐butylcyclohexane with singlet oxygen, nitrosyl hydride, nitrosoformaldehyde, 4‐phenyl‐1,2,4‐triazol‐3,5‐dione, diethyl azodicarboxylate and methyl propiolate . J. Chem. Soc., Perkin Trans. 2 , 2 : 721 – 734 . and references therein
   Google Scholar
• Ohashi , S. , Leong , K. , Matyjaszewski , K. and Butler , G. B. 1980 . Ene reaction of triazolinediones with alkenes, 1: Structure and properties of products . J. Org. Chem. , 45 ( 17 ) : 3467 – 3471 .
   Google Scholar
• Schenck , G. O. , Gollnick , K. and Neumüller , O.‐A. 1957 . Darstellung von Steroid‐hydroperoxyden Mittels phototoxischer Photosensibilisatoren . Justus Liebigs Ann. Chem. , 603 : 46 – 59 .
   Google Scholar
• Schenck , G. O. 1957 . Aufgaben und Möglichkeiten der präparativen Strahlenchemie . Angew. Chem. , 69 ( 18/19 ) : 579 – 599 .
   Google Scholar
• Schenck , G. O. and Neumüller , O.‐A. 1958 . Synthese tertiärer Steroid‐hydroperoxyde, insbesondere des Δ6‐Allopregnen‐3β‐ol‐20‐on‐5α‐hydroperoxyds . Justus Liebigs Ann. Chem. , 618 : 194 – 201 .
   Google Scholar
• Schenck , G. O. , Neumüller , O.‐A. and Eisfeld , W. 1958 . Δ5‐Steroid‐7α‐hydroperoxyde und ‐7‐ketone durch Allylumlagerung von Δ6‐Steroid‐5α‐hydroperoxyden . Justus Liebigs Ann. Chem. , 618 : 202 – 210 .
   Google Scholar
• Beckwith , A. L. J. , Davies , A. G. , Davison , I. G. E. , Maccoll , A. and Mruzek , M. H. 1989 . The mechanisms of the rearragments of allylic hydroperoxides: 5α‐hydroperoxy‐3β‐hydroxycholes‐6‐ene and 7α‐hydroperoxy‐3β‐hydroxycholes‐6‐ene and 7α‐hydroperoxy‐3β‐hydroxycholest‐5‐ene . J. Chem. Soc., Perkin Trans. 2 , : 815 – 824 .
   Google Scholar
• Ohloff , G. 1975 . Singlet oxygen: A reagent in organic synthesis . Pure Appl. Chem. , 43 : 481 – 502 .
   Web of Science ®Google Scholar
• Dang , H.‐S. , Davies , A. G. and Schiesser , C. H. 1990 . Allylic hydroperoxides formed by singlet oxygenation of cholest‐5‐en‐3‐one . J. Chem. Soc., Perkin Trans. 1 , : 789 – 794 .
   Google Scholar
• Dang , H.‐S. and Davies , A. G. 1992 . Ene reactions of allylically stannylated cholestenes: Singlet oxygenation of 7α‐triphenylstannylcholest‐5‐en‐3β‐ol, and of 7α‐triphenylstannyl‐ and 7α‐tributylstannyl‐choles‐5‐ene‐3‐one, and the rearrangement of 5α‐tributylstannylperoxy‐3β‐benzoyloxycholest‐6‐ene and of 7α‐tributylstannylperoxy‐3β‐benzoyloxycholst‐5‐ene . J. Chem. Soc., Perkin Trans. 2 , : 1095 – 1101 .
   Google Scholar
• Sridhar , R. and Floyd , R. A. 1982 . An eletron paramagnetic resonance study of the reaction of nitrosobenzene with cholesterol . Can. J. Chem. , 60 : 1574 – 1576 .
   Google Scholar
• Perrin , D. D. and Armarego , W. L. F. 1989 . Purification of Laboratory Chemicals , 3rd edition Oxford : Pergamon Press .
   Google Scholar