Bifunctionalized Allenes, VII: Two Methods for One‐Pot Synthesis of Sulfonyl‐Functionalized Allenecarboxylates and Phosphorylated Allenes

References

• Christov , V. C. and Prodanov , B. 2004 . Bifunctionalized allenes, VI: Synthesis of 3‐sulfinylfuran‐2(5H)‐ones and 5H‐1,2‐oxathiole‐3‐carboxylate 2‐oxides by bromination of 2‐sulfinyl‐2,3‐alkadienoates . Synth. Commun. , 34 : 1577 – 1588 . For Part VI, see
   Web of Science ®Google Scholar
• Patai , S. 1980 . The Chemistry of Ketenes, Allenes and Related Compounds New York : John Wiley & Sons .
   Google Scholar
• Landor , S. R. 1982 . The Chemistry of the Allenes London : Academic Press .
   Google Scholar
• Pasto , D. 1984 . J. Recent developments in allene chemistry. Tetrahedron , 40 : 2805
   Google Scholar
• Schuster , H. F. and Coppola , G. M. 1988 . Allenes in Organic Synthesis New York : John Wiley & Sons .
   Google Scholar
• Zimmer , R. 1993 . Alkoxyallenes—building blocks in organic synthesis . Synthesis , : 165 – 178 .
   Google Scholar
• Elsevier , C. J. 1995 . Methods of Organic Chemistry (Houben‐Weyl) Edited by: Helmchen , R. W. , Mulzer , J. and Schaumann , E. Vol. E21a , 537 – 566 . Stuttgart : Thieme .
   Google Scholar
• Krause , N. and Hashmi , A. S. K. 2004 . Modern Allene Chemistry Vol. 1–2 , Weinheim : Wiley‐VCH .
   Google Scholar
• Caserio , M. C. 1970 . “ Selectivity in addition reactions of allenes ” . In Selective Organic Transformations Edited by: Thyagarajan , B. S. 239 – 298 . New York : John Wiley & Sons .
   Google Scholar
• Jacobs , T. L. 1982 . “ Electrophilic addition to allenes ” . In The Chemistry of the Allenes Edited by: Landor , S. R. Vol. 2 , 417 – 509 . London : Academic Press .
   Google Scholar
• Smadja , W. 1983 . Electrophilic addition to allenic derivatives: Chemo‐, regio‐, and stereochemistry and mechanisms . Chem. Rev. , 83 : 263
   Web of Science ®Google Scholar
• Ma , S. M. 2004 . “ Ionic additions to allenes ” . In Modern Allene Chemistry Edited by: Krause , N. and Hashmi , A. S. K. Vol. 2 , 595 – 684 . Weinheim : Wiley‐VCH . chap. 10
   Google Scholar
• Jacobs , T. L. , Macomber , R. and Zucker , D. 1967 . Addition reactions of allenes, III: 2,4‐Dinitrobenzenesulfenyl chloride and bromine . J. Am. Chem. Soc. , 89 : 7001 – 7005 .
   Web of Science ®Google Scholar
• Toda , F. , Komora , T. and Akagi , K. 1968 . A new bromoallene alcohol: Its isolation and reaction . Bull. Chem. Soc. Jpn. , 41 : 1493
   Google Scholar
• Hoft , S. and Brandsma , L. 1969 . Acid‐catalyzed ring closure of 1‐methoxy‐or 1‐methylthio‐1‐(α‐ or β‐hydroxyalkyl)allenes . Rec. Trav. Chim. Pays‐Bas , 88 : 845 – 850 .
   Google Scholar
• Gelin , R. , Gelin , S. and Albrand , M. 1972 . Isomerisation en milieu acide d'alcools α‐alleniques . Bull. Soc. Chim. Fr. , : 720 – 723 .
   Google Scholar
• Gelin , R. , Gelin , S. and Albrand , M. 1972 . Oxymercuration‐demercuration d'alcools α‐alleniques . Bull. Soc. Chim. Fr. , : 1946 – 1949 .
   Google Scholar
• Olsson , L.‐I. and Claesson , A. 1979 . Synthesis of 2,5‐dihydrofurans and 5,6‐dihydro‐2H‐pyrans by silver(I)‐catalyzed cyclization of allenic alcohols . Synthesis , : 743 – 745 .
   Google Scholar
• Beaulieu , P. L. , Morisset , V. M. and Garratt , D. G. 1980 . The synthesis of 2,5‐dihydrofurans from α‐allenic alcohols . Tetrahedron Lett. , 21 : 129 – 132 .
   Google Scholar
• Marshal , J. A. and Wang , X. 1990 . [2,3]‐Wittig rearrangements of nonracemic (propargyloxy)acetic acids and esters: Synthesis of optically active 2,5‐dihydrofurans . J. Org. Chem. , 55 : 2995 – 2996 .
   Google Scholar
• Marshal , J. A. and Wang , X. 1991 . Synthesis of enantioenriched α‐hydroxy‐α‐allenylacetic acids by [2,3]‐Wittig rearrangement of α‐(propargyloxy)acetates . J. Org. Chem. , 56 : 4913 – 4918 .
   Google Scholar
• Marshal , J. A. and Pinney , K. G. 1993 . Stereoselective synthesis of 2,5‐dihydrofurans by sequential SN2′ cleavage of alkynyloxiranes and silver(I)‐catalyzed cyclization of the allenylcarbinol products . J. Org. Chem. , 58 : 7180 – 7184 .
   Google Scholar
• Ma , S. and Gao , W. 2000 . Efficient synthesis of 4‐(2′‐alkenyl)‐2,5‐dihydrofurans via PdCl2‐catalyzed coupling‐cyclization reaction of 2,3‐allenols with allylic halides . Tetrahedron Lett. , 41 : 8933 – 8936 .
   Web of Science ®Google Scholar
• Krause , N. , Laux , M. and Hoffman‐Roder , A. 2000 . New methods for the stereoselective synthesis of 2‐hydroxy‐3,4‐dienoates and functionalized 2,5‐dihydrofurans . Tetrahedron Lett. , 41 : 9613 – 9616 .
   Web of Science ®Google Scholar
• Hoffman‐Roder , A. and Krause , N. 2001 . Gold(III) chloride catalyzed cyclization of α‐hydroxyallenes to 2,5‐dihydrofurans . Org. Lett. , 3 : 2537 – 2538 .
   PubMedGoogle Scholar
• Krause , N. , Hoffman‐Roder , A. and Canisius , J. 2002 . From amino acids to dihydrofurans: Functionalized allenes in modern organic synthesis . Synthesis , : 1759 – 1774 .
   Google Scholar
• Kohler , E. P. and Whicher , W. J. 1940 . Optically active α,γ‐diphenyl‐α‐carbomethoxy‐γ‐naphthylallene . J. Am. Chem. Soc. , 62 : 1489 – 1490 .
   Google Scholar
• Aksnes , G. and Froeyen , P. 1968 . Study of the applicability of the Wittig reaction in synthesis of allenes . Acta Chim. Scand. , 22 : 2347 – 2347 .
   Google Scholar
• Shingu , K. , Hagishita , S. and Nakagawa , M. 1967 . The determination of the absolute configurations of some phenylallenecarboxylic acids . Tetrahedron Lett. , : 4371 – 4374 .
   Google Scholar
• Kresze , G. , Runge , W. and Ruch , E. 1972 . Zur stereochemie von allenen, I: Darstellung und optische spaltung einer gruppe von allenic carbonsauren . Liebigs Ann. Chem. , 756 : 112 – 127 .
   Google Scholar
• Musierowicz , S. , Wroblewski , A. E. and Krawczyk , H. 1975 . Stereochemistry of P‐chiral phosphinylacetic acid esters I: Asymmetric synthesis of substituted alkadiene‐1,2‐carboxylic‐1 and γ‐chiral α,β‐unsaturated carboxylic acid esters . Tetrahedron Lett. , : 437 – 440 .
   Google Scholar
• Kresze , G. , Kloimstein , W. L. and Runge , W. 1976 . Stereochemie von allenen, III: Cyclisierungreaktionen chiraler 3‐phenylallencarbonsauren . Liebigs Ann. Chem. , : 979 – 986 .
   Google Scholar
• Musierowicz , S. and Wroblewski , A. E. 1978 . Optically active α,β‐unsaturated γ‐lactones: Stereospecific transformation of allene carboxylic acids . Tetrahedron , 34 : 461 – 465 .
   Google Scholar
• Gill , G. B. and Idris , M. S. H. 1985 . Synthesis of α,β‐unsaturated butenolides from allenic acids . Tetrahedron Lett. , 26 : 4811 – 4814 .
   Google Scholar
• Marshal , J. A. , Wallace , E. M. and Soan , P. S. 1995 . Total synthesis of the pseudopterane (±)‐kallolide B . J. Org. Chem. , 60 : 796 – 797 .
   Google Scholar
• Ma , S. , Pan , F. , Hao , X. and Huang , X. 2004 . Reaction of PhSeCl or PhSCl with 2,3‐allenoic acids: An efficient synthesis of β‐organoselenium or β‐organosulfur substituted butenolides . Synlett , : 85 – 88 .
   Google Scholar
• Horner , L. and Binder , V. 1972 . Zur chemie der allensulfoxide . Liebigs Ann. Chem. , 757 : 33 – 68 .
   Google Scholar
• Braverman , S. and Reisman , D. 1977 . Electrophilic fragmentation‐cyclization of various allenic esters . Tetrahedron Lett. , : 1753 – 1756 .
   Google Scholar
• Braverman , S. and Reisman , D. 1977 . An unexpected sulfone to sulfinate transformation: Electrophilic fragmentation‐cyclization of diallenic sulfones and propargylic allenesulfinates to α,β‐unsaturated γ‐sultines . J. Am. Chem. Soc. , 99 : 605 – 607 .
   Web of Science ®Google Scholar
• Braverman , S. and Duar , Y. 1983 . Stereochemistry of the electrophilic fragmentation‐cyclization of allenic sulfones and sulfinates: Stereoselective synthesis of chiral α,β‐unsaturated γ‐sultines . J. Am. Chem. Soc. , 105 : 1061 – 1063 .
   Web of Science ®Google Scholar
• Angelov , C. M. 1983 . Five‐membered heterocyclization of phosphorus‐containing allenes by their reaction with electrophiles—possibilities and restrictions . Phosphorus Sulfur Relat. Elem. , 15 : 177
   Web of Science ®Google Scholar
• Khusainova , N. G. and Pudovik , A. N. 1987 . Phosphorylated allenes: Synthesis and reactions . Russ. Chem. Rev. , 56 : 975
   Google Scholar
• Alabugin , I. V. and Brel , V. K. 1997 . Phosphorylated allenes: Structure and interaction with electrophiles . Russ. Chem. Rev. , 66 : 205
   Google Scholar
• See Ref. [6a]
   Google Scholar
• Baudin , J.‐B. , Julia , S. A. and Wang , Y. 1989 . Substituted 4‐(1′,2′‐alkadienesulphinyl)‐morpholines; preparation and hydrolytic desulphinylation into the corresponding alkynes . Tetrahedron Lett. , 30 : 4965 – 4968 .
   Google Scholar
• Baudin , J.‐B. , Bkouche‐Waksman , I. , Julia , S. A. , Pascard , C. and Wang , Y. 1991 . Stereochemical course of the [2,3]‐sigmatropic rearrangement of substituted propargyl N,N‐dialkylamidosulfoxylates: X‐ray molecular structure of [S*, (S)R*]‐4‐[(1,4,4‐trimethyl‐1,2‐pentadienyl)sulfinyl]‐morpholine . Tetrahedron , 47 : 3353 – 3364 .
   Google Scholar
• Wang , X. , Ni , Z. , Lu , X. , Hollis , A. , Banks , H. , Rodriguez , A. and Padwa , A. 1993 . [2,3]‐Sigmatropic rearrangement of β‐phenylsulfonyl propargylic sulfenates as a method for preparing 1,4‐bis(phenylsulfonyl)‐1,3‐butadienes . J. Org. Chem. , 58 : 5377 – 5385 .
   Google Scholar
• Braverman , S. and Mechoulam , H. 1967 . Rearrangement of propargylic benzenesulfinates . Israel J. Chem. , 5 : 71 – 75 .
   Web of Science ®Google Scholar
• Smith , G. and Stirling , C. J. M. 1971 . Intramolecular reactions, part IX: Stereochemistry and mechanism of the rearrangement of acetylenic esters of sulphinic and sulphenic acids to allenes . J. Chem. Soc. C , : 1530 – 1535 .
   Google Scholar
• Braverman , S. , van Asten , P. F. T. M. , van der Linden , J. B. and Zwanenburg , B. 1991 . A novel synthesis of thiophenes from allenic sulfones involving α,β‐unsaturated sulfines as intermediates . Tetrahedron Lett. , 31 : 3867 – 3870 .
   Web of Science ®Google Scholar
• Brandsma , L. and Verkruijsse , H. D. 1981 . Synthesis of Acetylenes, Allenes and Cumulenes Amsterdam : Elsevier .
   Google Scholar
• Braverman , S. 1988 . “ Rearrangements involving sulfoxides ” . In The Chemistry of Sulphones and Sulphoxides Edited by: Patai , S. , Rappoport , Z. and Stirling , C. J. M. 665 – 716 . New York : John Wiley & Sons . chaps. 13
   Google Scholar
• Braverman , S. 1988 . “ Rearrangements involving sulfoxides ” . In In The Chemistry of Sulphones and Sulphones Edited by: Patai , S. , Rappoport , Z. and Stirling , C. J. M. 717 – 757 . New York : John Wiley & Sons . chap. 14
   Google Scholar
• Bestmann , H. J. and Hartung , H. 1963 . Synthesis of alkyl 2,3‐alkadienoates by Wittig reaction . Angew. Chem., Int. Ed. Engl. , 2 : 214
   Google Scholar
• See Ref. [5b]
   Google Scholar
• Miesch , M. 2003 . Synthesis of α‐allenic esters (acids) . Synthesis , : 746 – 752 . and references cited therein
   Google Scholar
• Coppe‐Motte , G. , Borghese , A. , Janousek , Z. , Merenyi , R. and Viehe , H. G. 1986 . Captodative substitution effect in [2+2] cycloadditions between allenes and olefins . NATO ASI Ser., Ser. C , 189 : 371 – 374 . Chem. Abstr. 1987, 107, 175273w
   Google Scholar
• Conrads , M. and Mattay , J. 1991 . Convenient methods for the preparation of sulfur substituted allenecarboxylates . Synthesis , : 11
   Google Scholar
• Padwa , A. , Bullock , W. H. , Norman , B. H. and Perumattam , J. 1991 . (Nitroaryl)sulfinyl‐substituted allenes: Novel and convenient propargyl alcohol synthons in 4+2 cycloaddition chemistry . J. Org. Chem. , 56 : 4252 – 4259 .
   Google Scholar
• Ref. 2e
   Google Scholar
• Hoff , S. , Brandsma , L. and Arens , J. R. 1968 . Preparation, metallation and alkylation of allenyl ethers . Recl. Trav. Chim. Pays‐Bas , 87 : 916 – 924 .
   Google Scholar
• Hoff , S. , Brandsma , L. and Arens , J. R. 1968 . Some conversions of allenyl ethers . Recl. Trav. Chim. Pays‐Bas , 87 : 1179 – 1184 .
   Google Scholar
• Zimmer , R. and Reissig , H.‐U. 1991 . Synthesis of 6H‐1,2‐oxazines by hetero Diels–Alder reactions of nitroso alkenes towards methoxyallenes . Liebigs Ann. Chem. , : 553 – 562 .
   Google Scholar
• Hormuth , S. and Reissig , H.‐U. 1991 . Diastereoselective additions of lithiated methoxyallene towards chiral aldehydes . Synlett , : 179 – 180 .
   Google Scholar
• Tsuboi , S. , Kuroda , H. , Takatsuka , S. , Fukawa , T. , Sakai , T. and Utaka , M. 1993 . A new aldol condensation of α‐allenic esters with aldehydes, including a one‐pot synthesis of enyne compounds . J. Org. Chem. , 58 : 5952 – 5957 .
   Web of Science ®Google Scholar
• Brandsma , L. , Wijers , H. E. and Arens , J. R. 1963 . Chemistry of acetylenic ethers. Allenyl thioethers from alkynyl thioethers . Recl. Trav. Chim. Pays‐Bas , 82 : 1040 – 1046 .
   Google Scholar
• see Ref. [6a]
   Google Scholar
• see Ref. [8b]
   Google Scholar
• see Ref. [9c]
   Google Scholar
• Horner , L. and Binder , V. 1971 . Zur chemie der allenphosphinoxide . Phosphorus , 1 : 17 – 22 .
   Google Scholar
• Macomber , R. S. , Krudy , G. A. and Amer , M. A. 1983 . Reactions of oxaphospholenes, 2: Hydrolysis of neopentyl esters, phenyl esters, and amides . J. Org. Chem. , 48 : 1420 – 1424 .
   Web of Science ®Google Scholar
• Macomber , R. S. and Hemling , T. C. 1985 . 139: A Horner–Emmons approach to cumulatrienes . Israel J. Chem. , 26 : 136 – 139 .
   Web of Science ®Google Scholar
• Macomber , R. S. and Bauer , P. D. 1978 . Synthetic approaches to molecules with sterically hidden functional groups . J. Chem. Res., Synop. , : 194 – 195 .
   Google Scholar
• Macomber , R. S. and Hemling , T. C. 1986 . Synthetic approaches to molecules with sterically hidden functional groups, 2: Bicyclo[8.8.2]eicosa‐1(19),10(20),19‐triene: The first bicyclic cumulatriene . J. Am. Chem. Soc. , 108 : 343 – 344 .
   Google Scholar
• Christov , V. C. and Prodanov , B. 2000 . Synthesis of 1‐substituted phosphorylated allenes . Phosphorus, Sulfur Silicon Relat. Elem. , 166 : 265 – 273 .
   Web of Science ®Google Scholar
• Christov , V. C. , Prodanov , B. and Nikolova , R. 2000 . One‐pot synthesis of 2‐substituted allenecarboxylates . Phosphorus, Sulfur Silicon Relat. Elem. , 166 : 275 – 281 .
   Web of Science ®Google Scholar
• Christov , V. C. and Prodanov , B. 2000 . Bifunctionalized allenes, part III: Bromination of 1‐substituted phosphorylated allenes . Phosphorus, Sulfur Silicon Ralat. Elem. , 166 : 243 – 249 .
   Web of Science ®Google Scholar
• Christov , V. C. and Prodanov , B. 2002 . Bifunctionalized allenes, part IV: 1,2λ5‐Oxaphosphole‐3‐carboxylates and 3‐phosphoryl‐2(5H)‐furanones from 2‐phosphoryl‐2,3‐alkadienoates . Heterocycl. Commun. , 8 : 349 – 354 .
   Web of Science ®Google Scholar
• Christov , V. C. and Prodanov , B. 2002 . Bifunctionalized allenes, part V: 3‐Sulfinyl‐2,5‐dihydro‐1,2λ5‐oxaphosphol‐2‐ones and 3‐phosphoryl‐1,2λ4‐oxathiol‐2(5H)‐ones from 1‐sulfinyl‐substituted phosphorylated allenes . Heterocycles , 57 : 1777 – 1780 .
   Web of Science ®Google Scholar
• see Ref. [1]
   Google Scholar
• Boisselle , A. P. and Meinhardt , N. A. 1962 . Acetylene‐allene rearrangements reactions of trivalent phosphorus chlorides with α‐acetylenic acohols and glycols . J. Org. Chem. , 27 : 1828 – 1833 .
   Web of Science ®Google Scholar
• Angelov , C. M. , Mikhailova , T. S. , Ignat'ev , V. M. , Dogadina , A. V. and Ionin , B. I. 1979 . Synthesis of 1,2‐alkadienephosphonic acids derivatives . Comp. Rend. Acad. Bulg. Sci. , 32 : 619 Chem. Abstr. 1979, 92, 22563 m
   Google Scholar