Trifunctionalized allenes. Part III. Electrophilic cyclization and cycloisomerization of 4-phosphorylated 5-hydroxypenta-2,3-dienoates: An expedient synthetic method to construct 2,5-dihydro-1,2-oxaphospholes, furan-2(5H)-ones and 2,5-dihydrofurans

References

• (a) Schuster, H. F.; Coppola, G. M. Allenes in Organic Synthesis; Wiley: New York, 1984; (b) Krause, N.; Hashmi, A. S. K., Eds. Modern Allene Chemistry; Wiley-VCH: Weinheim, 2004; (c) Brasholz, M.; Reissig, H.-U.; Zimmer, R. Sugars, Alkaloids, and Heteroaromatics: Exploring Heterocyclic Chemistry with Alkoxyallenes. Acc. Chem. Res. 2009, 42, 45–56. DOI: 10.1021/ar800011h. (d) Ma, S. Electrophilic Addition and Cyclization Reactions of Allenes. Acc. Chem. Res. 2009, 42, 1679–1688. DOI: 10.1021/ar900153r. (e) Yu, S.; Ma, S. Allenes in Catalytic Asymmetric Synthesis and Natural Product Syntheses. Angew. Chem. Int. Ed. 2012, 51, 3074–3112. DOI: 10.1002/anie.201101460.
   Google Scholar
• Hoffmann-Röder, A.; Krause, N. Synthesis and Properties of Allenic Natural Products and Pharmaceuticals. Angew. Chem. Int. Ed. 2004, 43, 1196–1216. DOI: 10.1002/anie.200300628.
   PubMed Web of Science ®Google Scholar
• (a) Yu, F.; Lian, X.; Ma, S. Pd-Catalyzed Regio- and Stereoselective Cyclization − Heck Reaction of Monoesters of 1,2-Allenyl Phosphonic Acids with Alkenes. Org. Lett. 2007, 9, 1703–1706. DOI: 10.1021/ol0703478. (b) Yu, F.; Lian, X.; Zhao, J.; Yu, Y.; Ma, S. CuX2-Mediated Halolactonization Reaction of Monoesters of 1,2-Allenyl Phosphonic Acids and Their Suzuki Cross-Coupling Reaction. J. Org. Chem. 2009, 74, 1130–1134. DOI: 10.1021/jo802051r. (c) Li, P.; Liu, Z.-J.; Liu, J.-T. Iodocyclization of Trifluoromethylallenic Phosphonates: Am Efficient Approach to Trifluoromethylated Oxaphospholenes. Tetrahedron 2010, 66, 9729–9732. DOI: 10.1016/j.tet.2010.10.040. (d) Xin, N.; Ma, S. Efficient Synthesis of 4‐Halo‐2,5‐dihydro‐1,2‐oxaphosphole 2‐Oxides from 1,2‐Allenylphosphonates and CuX2 and Subsequent Suzuki Cross‐Coupling of the C–Cl Bonds. Eur. J. Org. Chem. 2012, 3806–3817. DOI: 10.1002/ejoc.201200228. (e) Fourgeaud, P.; Volle, J.-N.; Vors, J.-P.; Bekro, Y.-A.; Pirat, J.-L.; Virieux, D. 5-H-1,2-Oxaphosphole 2-Oxides, Key Building Blocks for Diversity Oriented Chemical Libraries. Tetrahedron 2016, 72, 7912–7925. DOI: 10.1016/j.tet.2016.10.011. (f) Essid, I.; Laborde, C.; Legros, F.; Sevrain, N.; Touil, S.; Rolland, M.; Ayad, T.; Volle, J.-N.; Pirat, J.-L.; Virieux, D. Phosphorus-Containing Bis-allenes: Synthesis and Heterocyclization Reactions Mediated by Iodine or Copper Dibromide. Org. Lett. 2017, 19, 1882–1885. DOI: 10.1021/acs.orglett.7b00648.
   PubMed Web of Science ®Google Scholar
• (a) Wua, C.; Yeb, F.; Wub, G.; Xub, S.; Deng, G.; Zhang, Y.; Wang, J. Synthesis of Allenylphosphonates through Cu(I)-Catalyzed Coupling of Terminal Alkynes with Diazophosphonates. Synthesis 2016, 48, 751–760. DOI: 10.1055/s-0035-1561298. (b) Yang, J.; Zhang, M.; Dong, C.; Han, L.-B.; Shen, R. Solvent-Free Zn(OTf)2-Catalyzed Dehydrative Cross Coupling of Propargyl Alcohols with Diarylphosphine Oxides to Afford Allenylphosphine Oxides, Phosphorus Sulfur Silicon Relat. Elem. 2018, 193, 691–696; DOI: 10.1080/10426507.2018.1490281. (c) Shen, R.; Luo, B.; Yang, J.; Zhang, L.; Han, L.-B. Convenient Synthesis of Allenylphosphoryl Compounds via Cu-catalysed Couplings of P(O)H Compounds with Propargyl Acetates. Chem. Commun. 2016, 52, 6451–6454. DOI: 10.1039/C6CC02563C. (d) Shen, R.; Yang, J.; Zhang, M.; Han, L.-B. Silver‐Catalyzed Atom‐Economic Hydrophosphorylation of Propargyl Epoxides: An Access to 4‐Phosphoryl 2,3‐Allenols and Stereodefined 1‐Phosphoryl 1,3‐Dienes. Adv. Synth. Catal. 2017, 359, 3626–3637. DOI: 10.1002/adsc.201700421. (e) Shen, R.; Yang, J.; Zhao, H.; Feng, Y.; Zhang, L.; Han, L.-B. Cu-Catalyzed Hydrophosphorylative Ring Opening of Propargyl Epoxides: Highly Selective Access to 4-Phosphoryl 2,3-Allenols. Chem. Commun. 2016, 52, 11959–11962. DOI: 10.1039/C6CC05428E. (f) Kumara Swamy, K. C.; Phani Pavan, M.; Anitha, M.; Gangadhararao, G. New Addition and Cyclization Reactions Involving Phosphorus Based Allenes. Phosphorus Sulfur Silicon Relat. Elem. 2018, 193, 691–696; DOI: 10.1080/10426507.2017.1417302. (g) Fourgeaud, P.; Volle, J.-V.; Vors, J.-P.; Bekro, Y.-A.; Pirat, J.-L.; Virieux, D. 5-H-1,2-Oxaphosphole 2-oxides, Key Building Blocks for Diversity Oriented Chemical Libraries, Tetrahedron 2016, 72, 7912–7925. DOI: 10.1016/j.tet.2016.10.011. (h) Sajna, K. V.; Kotikalapudi, R.; Chakravarty, M.; Bhuvan Kumar, N. N.; Kumara Swamy, K. C. Cycloaddition Reactions of Allenylphosphonates and Related Allenes with Dialkyl Acetylenedicarboxylates, 1,3-Diphenylisobenzofuran, and Anthracene. J. Org. Chem. 2011, 76, 920–938. DOI: 10.1021/jo102240u. (i) Srinivas, V.; Sajna, K. V.; Kumara Swamy, K. C. To Stay as Allene or Go Further? Synthesis of Novel Phosphono-heterocycles and Polycyclics via Propargyl Alcohols. Chem. Commun. 2011, 47, 5629–5631. DOI: 10.1039/C1CC10230C. (j) Gangadhararao, G.; Kumara Swamy, K. C. Unusual Nitrogen Based Heterocycles via Allenic Intermediates from the Reaction of Propargyl Alcohols with P(III) Substrates. Tetrahedron 2014, 70, 2643–2653; DOI: 10.1016/j.tet.2014.02.064. (k) Kumara Swamy, K. C.; Mandala Anitha, M.; Gangadhararao, G.; Rama Suresh, R. Exploring Allene Chemistry Using Phosphorus-based Allenes as Scaffolds. Pure Appl. Chem. 2017, 89, 367–368. DOI: 10.1515/pac-2016-0907. (l) Kumara Swamy, K. C.; Anitha, M.; Debnath, S.; and Shankar, M. Reactivity of Allenylphosphonates/Allenylphosphine Oxides – Some New Addition/Cycloaddition and Cyclization Pathways. Pure Appl. Chem. 2019, 91. DOI: 10.1515/pac-2018-1111. (m) Bogachenkov, A. S.; Dogadina, A. V.; Boyarskaya, I. A.; Boyarskiy, V. P.; Vasilyev, A. V. Synthesis of 1,4-Dihydrophosphinoline 1-Oxides by Acid-promoted Cyclization of 1-(Diphenylphosphoryl)allenes. Org. Biomol. Chem. 2016, 1370–1381. DOI: 10.1039/C5OB02143J. (n) Lozovskiy, S. V.; Ivanov, A. Y.; Bogachenkov, A. S.; Vasilyev, A. V. 2,5-Dihydro-1,2-oxaphosphol-2-ium Ions, as Highly Reactive Phosphorus-Centered Electrophiles: Generation, NMR Study, and Reactions. Chem. Select. 2017, 2, 4505–4510. DOI: 10.1002/slct.201700637. (o) Essid, I.; Laborde, C.; Legros, F.; Sevrain, N.; Touil, S.; Rolland, M.; Ayad, T.; Volle, J.-N.; Pirat, J.-L.; Virieux, D. Phosphorus-Containing Bis-allenes: Synthesis and Heterocyclization Reactions Mediated by Iodine or Copper Dibromide, Org. Lett. 2017, 19, 1882–1885. DOI: 10.1021/acs.orglett.7b00648.
   Google Scholar
• Brel, V. K.; Belsky, V. K.; Stash, A. I.; Zavodnik, V. E.; Stang, P. J. Synthesis and Molecular Structure of New Unsaturated Analogues of Nucleotides Containing Six-Membered Rings. Eur. J. Org. Chem. 2005, 2005, 512–521. DOI: 10.1002/ejoc.200400523.
   Web of Science ®Google Scholar
• (a) Angelov, C. M. Reactivity of Sulfuryl Chloride in Reaction with 1,2- Alkadienephosphonates. Zh. Obshch. Khim. 1980, 50, 2448–2452. (b)
   Google Scholar
  Angelov, C. M.; Stoianov, N. M.; Ionin, B. I. Halogenation of 5-Methyl-1,3,4-Hexatriene-3-Phosphonic Dialkyl Esters. Zh. Obshch. Khim. 1982, 52, 178–181. (c)
   Google Scholar
  Angelov, Ch. M.; Christov, Ch. Z. Synthesis of 3-Vinyl-2,5-Dihidro-1,2-Oxaphophole-2-Oxides. Synthesis 1984, 664–667. DOI: 10.1055/s-1984-30926. (d)
   Google Scholar
  Yu, F.; Lian, X.; Zhao, J.; Yu, Y.; Ma, S. CuX2-Mediated Halolactonization Reaction of Monoesters of 1,2-Allenyl Phosphonic Acids and their Suzuki Cross-Coupling Reaction. J. Org. Chem. 2009, 74, 1130–1134. DOI: 10.1021/jo802051r. (e)
   PubMed Web of Science ®Google Scholar
  Angelov, C. M. Five-membered Heterocyclization of Phosphorus-containing Allenes by their Reaction with Electrophiles-Possibilities and Restrictions. Phosphorus Sulfur Silicon Relat. Elem. 1983, 15, 177–193. DOI: 10.1080/03086648308073293. (f)
   Web of Science ®Google Scholar
  Khusainova, N. G.; Pudovik, A. N. Phosphorylated Allenes. Methods of Synthesis and Properties. Russ. Chem. Rev. 1987, 56, 564–578. DOI: 10.1070/RC1987v056n06ABEH003290. (g)
   Google Scholar
  Alabugin, I. V.; Brel, V. K. Phosphorylated Allenes: Structure and Interaction with Electrophilic Reagents. Russ. Chem. Rev. 1997, 66, 205–224. DOI: 10.1070/RC1997v066n03ABEH000262. (h)
   Google Scholar
  Ma, S. Electrophilic Addition and Cyclization Reactions of Allenes. Acc. Chem. Res. 2009, 42, 1679–1688. DOI: 10.1021/ar900153r. (i)
   PubMed Web of Science ®Google Scholar
  Brel, V. K. Phosphonoallenes for Building Organophosphorus Derivatives. Heteroatom. Chem. 2006, 17, 547–556. DOI: 10.1002/hc.20275.
   Web of Science ®Google Scholar
• (a) Angelov, C. M.; Christov, C. Z.; Ionin, B. I. Chlorination of Tertiary Allenic Phosphine Oxides. Zh. Obshch. Khim. 1982, 52, 264–267. (b) Khusainova, N. G.; Naumova, L. V.; Berdnikov, E. A.; Pudovik, A. N. Interaction of Phosphorylated Allenes with Sulfenyl Chlorides. Zh. Obshch. Khim. 1982, 52, 1040–1046. [c] Enchev, D. D.; Angelov, C. M.; Krawchik, E.; Skowronska, A.; Michalski, J. 2,5-Dihydro-1,2-Oxaphospholene Derivatives by the Reaction of 1,2-Alkadienephosphonates and Phosphorus Pseudohalogenes. Phosphorus Sulfur Silicon Relat. Elem. 1991, 57, 249–253. DOI: 10.1080/10426509108038856.
   Google Scholar
• For reviews, see (a) Rao, Y. S. Chemistry of Butenolides. Chem. Rev. 1964, 64, 353–388. (b)
   Web of Science ®Google Scholar
  Rao, Y. S. Recent Advances in the Chemistry of Unsaturated Lactones. Chem. Rev. 1976, 76, 625–994. DOI: 10.1021/cr60303a004. (c)
   Web of Science ®Google Scholar
  Knight, D. W. Synthetic Approaches to Butenolides. Contemp. Org. Synth. 1994, 287–315. DOI: 10.1021/cr60230a002.
   Google Scholar
• (a) Kohler, E. P.; Whitcher, W. J. Optically Active α,γ-Diphenyl-α-carbomethoxy-γ-naphthylallene. J. Am. Chem. Soc. 1940, 62, 1489–1490. DOI: 10.1021/ja01863a044. (b)
   Google Scholar
  Asknes, G.; Froyen, P. Study of the Applicability of the Wittig Reaction in Syntheses of Allenes. Acta Chem. Scand. 1968, 22, 2347–2352. DOI: 10.3891/acta.chem.scand.22-2347. (c)
   Google Scholar
  Kresze, G.; Runge, W.; Ruth, E. Zur Stereochemie von Allenen, I. Darstellung und optische Spaltung einer Gruppe von Allencarbonsäuren. Liebigs Ann. Chem. 1972, 756, 112–127. DOI: 10.1002/jlac.19727560111. (d)
   Google Scholar
  Musierowicz, S.; Wroblewski, A.; Krawczyk, H. Stereochemistry of p-Chiral Phosphinylacetic Acid Esters I Asymmetric Synthesis of Substituted Alkadiene-1,2-carboxylic-1 and X-Chiral α, β-Unsaturated Carboxylic Acid Esters. Tetrahedron Lett. 1975, 437–440. DOI: 10.1016/S0040-4039(00)71887-9. (e)
   Web of Science ®Google Scholar
  Kresze, G.; Kloimstein, L.; Runge, W. Stereochemie von Allenen, III1) Cyclisierungsreaktionen Chiraler 3‐Phenylallencarbonsäuren. Liebigs Ann. Chem. 1976, 979–986. DOI: 10.1002/jlac.197619760602. (f)
   Google Scholar
  Gill, G. B.; Idris, M. S. H. Synthesis of α,β-Unsaturated Butenolides from Allenic Acids. Tetrahedron Lett.1985, 26, 4811–4814. DOI: 10.1016/S0040-4039(00)94958-X. (g)
   Web of Science ®Google Scholar
  Shingu, K.; Hagishita, S.; Nakagawa, M. The Determination of the Absolute Configurations of Some Phenylallenecarboxylic Acids. Tetrahedron Lett. 1967, 4371–4374. DOI: 10.1016/S0040-4039(01)89692-1. (h)
   Web of Science ®Google Scholar
  Ma, S.; Wu, S. CuX2-Mediated Cyclization Reaction of 2,3-Allenoic Acids. An Efficient Route to β-Halobutenolides. J. Org. Chem. 1999, 64, 9314–9317. (i) Ma, S.; Shi, Z.; Yu, Z. Synthesis of β-Halobutenolides and their Pd(0)-Catalyzed Cross-Coupling Reactions with Terminal Alkynes and Organozinc Reagents. A General Route to β-Substituted Butenolides and Formal Synthesis of cis-Whisky Lactone. Tetrahedron 1999, 55, 12137–12148. DOI: 10.1021/jo991574t. (j) Ma, S.; Wu, S. CuBr2-Mediated Direct Aqueous Bromolactonization of 2,3-Allenoates. An Efficient Access to β-Bromobutenolides. Tetrahedron Lett. 2001, 42, 4075–4077. DOI: 10.1016/S0040-4039(01)00634-7. (k) Ma, S.; Pan, F.; Hao, X.; Huang, X. Reaction of PhSeCl or PhSCl with 2,3-Allenoic Acids: An Efficient Synthesis of β-Organoselenium or β-Organosulfur Substituted Butenolides. Synlett 2004, 85–88. DOI: 10.1055/s-2003-43377. (l) Fu, C.; Ma, S. Efficient Preparation of 4‐Iodofuran‐2(5H)‐ones by Iodolactonisation of 2,3‐Allenoates with I2. Eur. J. Org. Chem. 2005, 3942–3945. DOI: 10.1002/ejoc.200500296. (m) Chen, G.; Fu, C.; Ma, S. Studies on Electrophilic Addition Reaction of 2,3-Allenoates with PhSeCl. Tetrahedron 2006, 62, 4444–4452. DOI: 10.1016/j.tet.2006.02.053. (n) Zhou, C.; Ma, Z.; Gu, Z.; Fu, C.; Ma, S. An Efficient Approach for Monofluorination via Aqueous Fluorolactonization Reaction of 2,3-Allenoic Acids with Selectfluor. J. Org. Chem. 2008, 73, 772–774. DOI: 10.1021/jo702409y.
   Web of Science ®Google Scholar
• Zimmer, R.; Dinesh, C. U.; Nandanan, E.; Khan, F. A. Palladium-Catalyzed Reactions of Allenes. Chem. Rev. 2000, 100, 3067–3125. DOI: 10.1021/cr9902796.
   PubMed Web of Science ®Google Scholar
• (a) Olsson, L.-I.; Claesson, A. Synthesis of 2,5-Dihydrofurans and 5,6-Dihydro-2H-pyrans by Silver(I)-Catalyzed Cyclization of Allenic Alcohols. Synthesis 1979, 743–745. DOI: 10.1055/s-1979-28825. (b) Nikam, S. S.; Chu, K. H.; Wang, K. K. The Cyclization of Trimethylsilyl-substituted a-Allenic Alcohols to 3-(trimethylsilyl)-2,5-dihydrofurans and their Facile Autoxidation to 3-(Trimethylsilyl)furans or 4-(Trimethylsilyl)-2(5H)-furanones. J. Org. Chem. 1986, 51, 745–747. DOI: 10.1021/jo00355a034. (c) Marshall, J. A.; Sehon C. A. Synthesis of Furans and 2,5-Dihydrofurans by Ag(I)-Catalyzed Isomerization of Allenones, Alkynyl Allylic Alcohols, and Allenylcarbinols. J. Org. Chem. 1995, 60, 5966–5968. DOI: 10.1021/jo00123a040. (d) Marshall, J. A.; Yu, R. H.; Perkins, J. F. Diastereo- and Enantioselective Synthesis of Allenylcarbinols through SE2’ Addition of Transient Nonracemic Propargylic Stannanes to Aldehydes. J. Org. Chem. 1995, 60, 5550–5555. DOI: 10.1021/jo00122a040.
   Google Scholar
• (a) Chilot, J.-J.; Doutheau, A.; Gore, J. Heterocyclisation de diols βγ-alleniques. Tetrahedron Lett. 1982, 23, 4693–4696. DOI: 10.1016/S0040-4039(00)85689-0. (b) Gelin, R.; Gelin, S.; Albrand, M. Oxymercuration Demercuration d’Alcools α-Alleniques. Bull. Soc. Chim. Fr. 1972, 1946–1949.
   Google Scholar
• (a) Uemura, K.; Shiraishi, D.; Noziri, M.; Inoue, Y. Preparation of Cyclic Carbonates from Alkadienols, CO2, and Aryl or Vinylic Halides Catalyzed by a Palladium Complex. Bull. Chem. Soc. Jpn. 1999, 72, 1063–1069. DOI: 10.1246/bcsj.72.1063. (b) Kang, S.-K.; Baik, T.-G.; Kulak, A. N. Palladium(0)-Catalyzed Coupling Cyclization of Functionalized Allenes with Hypervalent Iodonium Salts. Synlett 1999, 324–326. DOI: 10.1055/s-1999-2613. (c) Kang, S.-K.; Yamaguchi, T.; Pyun, S.- J.; Lee, Y.-T.; Baik, T.-G. Palladium-catalyzed Arylation of α-Allenic Alcohols with Hypervalent Iodonium Salts: Synthesis of Epoxides and Diol Cyclic Carbonates. Tetrahedron Lett. 1998, 39, 2127–2130. DOI: 10.1016/S0040-4039(98)00076-8.
   Web of Science ®Google Scholar
• (a) Ma, S.; Gao, W. Efficient Synthesis of 4-(20-Alkenyl)-2,5-dihydrofurans via PdCl2-catalyzed Coupling-cyclization Reaction of 2,3-Allenols with Allylic Halides. Tetrahedron Lett. 2000, 41, 8933–8936. DOI: 10.1016/S0040-4039(00)01585-9. (b) Ma, S.; Gao, W. Efficient Synthesis of 4-(2’-Alkenyl)-2,5-Dihydrofurans and 5,6-Dihydro-2H-pyrans via the Pd-Catalyzed Cyclizative Coupling Reaction of 2,3- or 3,4-Allenols with Allylic Halides. J. Org. Chem. 2002, 67, 6104–6112. DOI: 10.1021/jo0163997.
   Web of Science ®Google Scholar
• (a) Yoneda, E.; Kaneko, T.; Zhang, S.-W.; Onitsuka, K.; Takahashi, S. Ruthenium-Catalyzed Cyclic Carbonylation of Allenyl Alcohols. Selective Synthesis of χ- and δ-Lactones. Org. Lett. 2000, 2, 441–443. DOI: 10.1021/ol990377d. (b) Trost, B. M.; Pinkerton, A. B. A Ruthenium-Catalyzed Alkylative Cycloetherification. J. Am. Chem. Soc. 1999, 121, 10842–10843. DOI: 10.1021/ja9929537.
   PubMed Web of Science ®Google Scholar
• (a) Hoffmann-Roder, A.; Krause, N. The Golden Gate to Catalysis. Org. Biomol. Chem. 2005, 3, 387–391. DOI: 10.1039/B416516K. (b) Widenhoefer, R. A.; Han, X. Gold-Catalyzed Hydroamination of C–C Multiple Bonds. Eur. J. Org. Chem. 2006, 4555–4563. DOI: 10.1002/ejoc.200600399. (c) Hashmi, A. S. K.; Hutchings, G. J. Gold Catalysis. Angew. Chem. Int. Ed. 2006, 45, 7896–7936. DOI: 10.1002/anie.200602454. (d) Jimenez-Nunez, E.; Echavarren, A. M. Molecular Diversity through Gold Catalysis with Alkynes. Chem. Commun. 2007, 333–343. DOI: 10.1039/B612008C. (e) Gorin, D. J.; Toste, F. D. Relativistic Effects in Homogeneous Gold Catalysis. Nature 2007, 446, 395–403. DOI: 10.1038/nature05592. (f) Bongers, N.; Krause, N. Golden Opportunities in Stereoselective Catalysis. Angew. Chem. Int. Ed. 2008, 47, 2178–2181. DOI: 10.1002/anie.200704729.
   PubMed Web of Science ®Google Scholar
• (a) Hoffman-Roder, A.; Krause, N. Gold(III) Chloride Catalyzed Cyclization of α-Hydroxyallenes to 2,5-Dihydrofurans. Org. Lett. 2001, 3, 2537–2538. DOI: 10.1021/ol01620+. (b) Krause, N.; Hoffman-Roder, A.; Canisius, J. From Amino Acids to Dihydrofurans: Functionalized Allenes in Modern Organic Synthesis. Synthesis 2002, 1759–1774. DOI: 10.1055/s-2002-33707. (c) Deutsch, C.; Gockel, B.; Hoffmann-Roder, A.; Krause, N. Golden Opportunities in Stereoselective Catalysis: Optimization of Chirality Transfer and Catalyst Efficiency in the Gold-Catalyzed Cycloisomerization of α-Hydroxyallenes to 2,5-Dihydrofurans. Synlett 2007, 1790–1794. DOI: 10.1055/s-2007-982561.
   PubMed Web of Science ®Google Scholar
• (a) Brel, V. K. Synthesis and Cyclization of Diethylphosphono-Substituted α-Allenic Alcohols to 4-(Diethylphosphono)-2,5-Dihydrofurans. Synthesis 1999, 463–466. DOI: 10.1055/s-1999-3420. (b) Brel, V. K.; Abramkin, E. V. Cyclization of Allenyl Phosphonates to 3-Chloro-4-(Diethylphosphono)-2,5-Dihydrofurans Induced by CuCl2. Mendeleev Commun. 2002, 12, 64–66. DOI: 10.1070/MC2002v012n02ABEH001574.
   Google Scholar
• Ismailov, I. E.; Ivanov, I. K.; Christov, V. C. Trifunctionalized Allenes. Part I. A Convenient and Efficient Regioselective Synthesis of 4-Phosphorylated 5-Hydroxyalka-2,3-Dienoates. Bulg. Chem. Commun. Special Edition B 2017, 49, 33–41.
   Google Scholar
• (a) De la Mare, P. B. D.; Bolton, R. Electrophilic Addition to Unsaturated Systems; Elsevier: Amsterdam, The Netherlands, 1966; pp. 250–266. (b) Caserio, M. C. Selectivity in Addition Reactions of Allenes in Selective Organic Transformations; Thyagarajan, B. S., Ed.; John Wiley & Sons: New York, NY, 1970; pp. 239–299. (c) De la Mare, P. B. D.; Bolton, R. Electrophilic Addition to Unsaturated Systems; Elsevier: Amsterdam, The Netherlands, 1982; pp. 317–325. (d) Jacobs, T. L. Electrophilic Addition to Allenes in the Chemistry of the Allenes; Landor, S. R., Ed.; Academic Press: New York, 1982; Vol. 2, pp. 417–510. (e) Smadja, W. Electrophilic Addition to Allenic Derivatives: Selectivity, Regio- and Stereochemistry and Mechanisms. Chem. Rev. 1983, 83, 263–320. DOI: 10.1021/cr00055a003. (f) Ma, S. Ionic Addition to Allenes in Modern Allene Chemistry; Krause, N., Hashmi, A. S. K., Eds.; Wiley-VCH: Weinheim, Germany, 2004; Vol. 2, pp. 595–699.
   Google Scholar
• Baldwin, J. E. Rules for Ring Closure. J. Chem. Soc. Chem. Commun. 1976, 734–736. DOI: 10.1039/c39760000734.
   Google Scholar
• (a) Ivanov, I. K.; Parushev, I. D.; Christov, V. C. Bifunctionalized Allenes. Part XI. Competitive Electrophilic Cyclization and Addition Reactions of 4-Phosphorylated Allenecarboxylates. Heteroatom Chem. 2014, 25, 60–71. DOI: 10.1002/hc.21136. (b) Ismailov, I. E.; Ivanov, I. K.; Christov, V. C. Bifunctionalized Allenes. Part XV. Synthesis of 2,5-Dihydro-1,2-Oxaphospholes by Electrophilic Cyclization Reaction of Phosphorylated α-Hydroxyallenes. Molecules 2014, 19, 11056–11076. DOI: 10.3390/molecules190811056. (c) Christov, V. C.; Ismailov, I. E.; Ivanov, I. K. Bifunctionalized Allenes. Part XVI. Synthesis of 3-Phosphoryl-2,5-dihydrofurans by Coinage Metal-Catalyzed Cyclo-isomerization of Phosphorylated α-Hydroxyallenes. Molecules 2015, 20, 7263–7275. DOI: 10.3390/molecules20047263. (d) Hasanov, H. H.; Ivanov, I. K.; Christov, V. C. Bifunctionalized allenes. Part XXI. Electrophilic Cyclization аnd Addition Reactions of 3-(α- or β-Hydroxyalkyl)-allenephosphonates and -allenyl Phosphine Oxides. Phosphorus Sulfur Silicon Relat. Elem. 2018, 193, 611–619. DOI: 10.1080/10426507.2018.1487432. (e) Hasanov, H. H.; Ivanov, I. K.; Christov, V. C. Bifunctionalized allenes. Part XXII. Coinage Metal-catalyzed Cycloisomerization of Phosphorylated 3-(α- or β-Hydroxyalkyl)allenes to 2-Phosphoryl-2,5-dihydrofurans or 2-Phosphoryl-5,6-dihydro-2Н-pyrans. Phosphorus Sulfur Silicon Relat. Elem. 2018, 193, 797–805. DOI: 10.1080/10426507.2018.1515947. (f) Hasanov, H. H.; Ivanov, I. K.; Christov, V. C. Bifunctionalized allenes, Part XIX: Synthesis, Electrophilic Cyclization/addition, and Coinage Metal-catalyzed Cycloisomerization of Phosphorylated 3-(β-Hydroxy)allenes. Heteroatom Chem. 2017, 28, e21357. DOI: 10.1002/hc.21357.
   Web of Science ®Google Scholar
• Lecher, H.; Holschneider, F. Phenyl‐Schwefelchlorid. Ber. Dtsch. Chem. Ges. A/B. 1924, 57, 755–758. DOI: 10.1002/cber.19240570503.
   Google Scholar