Phosphorus Heterocycles II by Shigeru Sasaki (auth.), Raj K. Bansal (eds.)

By Shigeru Sasaki (auth.), Raj K. Bansal (eds.)

S. Sasaki: Heterophenes wearing Phosphorus practical teams as Key Structures.- D.D. Enchev: Synthesis and organic task of 2,5-Dihydro-1,2-Oxaphosphole-2-Oxide Derivatives.- D. Gudat: fresh advancements within the Chemistry of N -Heterocyclic Phosphines.- J. Drabowicz ∙ D. Krasowska ∙ A. Łopusiński ∙T.S.A. Heugebaert ∙ C.V. Stevens: chosen 5-membered Phosphorus Heterocycles Containing a Stereogenic Phosphorus.- G. Keglevich: 1-(2,4,6-Trialkylphenyl)-1 H -Phospholes with a Flattened P-Pyramid: Synthesis and Reactivity.- N. Gupta: contemporary Advances within the Chemistry of Diazaphospholes

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On the other hand, oxidation with excess mCPBA gave sulfone 29 as a stable product. ) P(O)(OEt)2 P(O)(OEt)2 E 13: E = S (53%) 14: E = Se (68%) excess E = S m CPBA (EtO)2(O)P (EtO)2(O)P P(O)(OEt)2 S O O 29 P(O)(OEt)2 (EtO)2(O)P (EtO)2(O)P P(O)(OEt)2 P(O)(OEt)2 E O 28: E = S 30: E = Se Scheme 29 Synthesis of tetraphosphorylthiophene and selenophene [39] Tetraphosphorylselenophene 14 was synthesized in a similar manner (Schemes 27 and 29). Sodium hydroselenide added to diphosphorylacetylene 22 to give tetraphosphoryldihydroselenophene 24.

The use of sulfur dioxide in this reaction promoted the formation of the oxaphosphole product (Scheme 35) [22, 44, 71–73, 87–92]. R Cl R S 1 R R2 Cl2P R1 RSCl RSCl R2 Cl2P O R S Cl2P Cl2P R O O Cl SR Cl 2 R1 R2 R1=R2=H RSCl R1 Cl2P Cl2P R2 O R1=R2=H RS R1 Cl2P O O SR Cl S Cl2P Cl2P SR Cl Cl O O Cl R1=R2=H SR SR Cl Cl2P O 1 R1 R2 O 2 R =R =Me SO2 SR SR Me Cl2P O O P C2H4Cl2, -5° - -8°C to room, 24h Cl O R1 R2 Scheme 35 2,4-Dichloro-2-oxo-1,2-oxaphosphol-2-oxide derivatives could be produced from the reaction of dialkylphosphorylsulphenyl chloride with 1,2-alkadienephosphonic dichlorides (Scheme 36) [87, 89].

Morita of Tohoku University for encouragement. References 1. Patai S (ed) (1974) The chemistry of the quinoid compounds, parts 1 and 2. Wiley, London 2. Patai S, Rappoport Z (eds) (1988) The chemistry of the quinoid compounds, vol 2, parts 1 and 2. Wiley, Chichester 3. Bock H, Mohmand S, Hirabayashi T, Maier G, Reisenauer HP (1983) Chem Ber 116:273 4. Raasch MS (1979) J Org Chem 44:632 5. Itoh T, Fujikawa K, Kubo M (1996) J Org Chem 61:8329 6. Suzuki R, Matsumoto K, Kurata H, Oda, M (2000) Chem Commun 1357 7.

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