Addition of nitryl iodide to 3 -d e o x y -1 , 2 : 5 , 6 -d i -0 -i s o p r o p y l i d e n e -3 -~r a n o s e (2), followed by treatment of the product with sodium borohydride, gave crystalline 3-deoxy-1,2:5,6-di-O-isopropylidene-3-C-nitromethyl-a-~-aofuranose (3); the branched-chain unsaturated sugar (2) was prepared by way of a Wittig reaction with 1,2:5,6-di-O-isopropylidene-a-o-ribo-hexofuran0s-3-ul0se (1). Acid-catalyzed hydrolysis of 3 afforded 3-deoxy-3-C-nitromethyl-D-allose, which exists predominantly in the P-D-furanose form (4).L'addition d'iodure de nitryle au 3-deoxy-1,2:5,6-di-O-isopropylid~ne-3-methylene-~-~-ribo-hexofuranose (2), le produit obtenu etant trait6 au borohydrure de sodium, donne le 3-desoxy-1,2:5,6-di-0-isopropylidene-3-C-nitromethyl-a-D-allofuranose cristallis6 (3); le sucre a double liaison exocyclique (2) a ete prepare par reaction de Wittig par le 1,2:5,6-di-O-isopropylidene-a-~-ribo-hexofuranos-3-ulose (1). L'hydrolyse catalysee par les acides de 3 conduit au 3-desoxy-3-C-nitromethyl-D-allose, qui existe de maniQe predominante sous la fornie J3-D-furanose (4).
FR~NCOIS-XAVIER GARKEAU and IRENEUSZ SZCZEREK. Can. J . Chem. 57.299! (i979). The near ultraviolet photolysis (h > 280 nm) of liquid cis-2-butene in the presence of hydrogen sulfide was shown to result in isomerization and addition reactions. The former was monitored by the formation of trans-2-butene as a function of time and hydrogen sulfide concentration. The latter was observed by the presence of s-butyl mercaptan and di-s-butyl sulfide as products. The total amount of addition products as well as the relative amounts of mercaptan and sulfide were determined as a function of time. Using the foregoing information the extent of the isomerization reaction was shown to be greater than that of the addition reaction during the course of the irradiation at a concentration ratio of H,S/cis-2-butene equal to 0.15.It was also shown that hydrogen sulfide was a more effective sensitizer than s-butyl mercaptan and di-s-butyl sulfide but less effective than di-s-butyl disulfide in the isomerization of liquid cis-2-butene. The extent of isomerization and addition reactions were shown to be greater starting with cis-2-butene than with trans-2-butene in the presence of hydrogen sulfide. En outre, le sulfure a'hydrogene s'est avere un sensibilisateur plus efficace que ie mercaptan de butyi-secondaire et le sulfure de di-butyi-secondaire mais moins efficace que le disulfure du dibutyl-secondaire dans l'isomerisation du cis-butene-2 liquide. Les reactions d'isomerisation et d'addition sont plus rapides en partant avec le cis-butene-2 que le trans-butene-2 en presence du sulfure d'hydrogene.
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