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By Elbertus Kruiswijk. Emedia

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By Elbertus Kruiswijk. Emedia

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Pharm. ), 1991, 324, 61. 5) O. Bozdağ; G. Ayhan-Kilcigil; M. Tunçbilek; R. Ertan, Turk. J. , 1999, 23, 163. COMMENTS : ANSCHÜTZ ANTHRACENE SYNTHESIS EXAMPLE : H Br 2 + Br Br AlCl3 Br H 51 MECHANISM : H Br Br Br Br AlCl3 H DISCONNECTION : H X + X X X H X = Cl, Br NOTES : The synthesis of anthracenes from benzene, 1,1,2,2-tetrachloroethane or 1,1,2,2-tetrabromoethane and aluminium trichloride. See also Friedel – Crafts and Nenitzescu acylation reactions. A. Anschütz; A. Angelbis, Ber. Dtsch. Chem.

Nagai; M. Hamaguchi, Org. Prep. Proced. , 1993, 25, 403. K. A. R. Nass; F. W. Bats; M. Bolte, Eur. J. Org. , 2001, 4705. COMMENTS : AMADORI REARRANGEMENT EXAMPLE : OH HO HO O OH H N H C18H37 HO HCl pyridine 38 HO O OH OH N H C18H37 MECHANISM : H H HO H H NRR1 OH H OH O CH2OH H+ R - H+ N H HO H H H H HO H H H H HO H H NRR1 OH H OH OH CH2OH R R1 H OH H HO H H H OH OH CH2OH H H HO HO H H NRR1 OH H OH H O CH2OH N R1 O H OH OH CH2OH H NRR1 H HO HO H H H2C H OH O CH2OH NRR1 H OH OH O DISCONNECTION : H H H NRR1 OH HO H H OH H OH CH2OH H H HO H H NRR1 OH H OH O CH2OH NOTES : N-Substituted glycosylamines derived from primary aromatic amines and certain other bases give 1-deoxy-1-amino-2ketoses slowly at room temperature or rapidly in hot ethanolic solutions in the presence of compounds containing active methylenic hydrogen atoms or in the presence of catalytic amounts of acids.

Coll. Vol. : 6, 634 1) R. Appel, Angew. , Int. Ed. , 1975, 14, 801. 2) H. Vorbrüggen; K. , 1981, 22, 4471. 3) H. Vorbrüggen; K. Krolikiewicz, Tetrahedron, 1993, 49, 9353. 4) A. Scheurer; P. Mosset; W. W. Saalfrank, Eur. J. Org. , 2001, 3067. S. K. , 2002, 43, 5419. 6) L. Desmaris; N. Percina; L. Cottier; D. , 2003, 44, 7589. W. C. B. Wagener, Tetrahedron, 2004, 60, 10943. COMMENTS : ARBUZOV REACTION (MICHAELIS – ARBUZOV) EXAMPLE : H3C (CH3CH2O)3P + CH3CH2Br neat 56 O P OEt OEt MECHANISM : (CH3CH2O)P OEt RCH2 P O CH2CH3 OEt RCH2-X X OEt EtO P CH3CH2X + O R DISCONNECTION : R1 O P OR OR R1 O P OR R RO OR P + RX OR R OR P + RX OR O R1 P R R R P R OR + RX NOTES : This reaction in its simplest form consists in the transformation of a trialkyl phosphite into a dialkylalkane phosphonate by warming with concentrated alkyl halide.

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