The Chemistry of Amino, Nitroso, Nitro and Related Groups, by Saul Patai

By Saul Patai

Natural compounds containing Nitrogen are of remarkable significance in biochemistry and in environmental structures. This quantity offers a valid advent into the actual chemistry of amino, nitroso, nitro and comparable practical teams.

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Extra resources for The Chemistry of Amino, Nitroso, Nitro and Related Groups, Supplement F2 Part 2

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The arylation of 2,3-dihydrofuran (38) with phenyl tri¯ate using BINAP (XXXI) as a chiral ligand gave 2-phenyl-2,3-dihydrofuran (42) with 967 ee. Addition of HÀPdÀX to the primary product 40 gives the intermediate 41, and b-elimination affords the dihydrofuran 42 with 967 ee in 717 yield as the major product in the presence of 1,8-bis(dimethylamino)naphthalene (39) as a base. Another dihydrofuran 40 with 677 ee was obtained in 77, showing that one enantiomer of 40 is converted to 42 with high selectivity [24].

Reactions with alkynes 47 Monosubstitution of acetylene itself to prepare terminal alkynes is not easy. Therefore, trimethylsilylacetylene (134) is used as a protected acetylene. After the coupling, the silyl group is removed by the treatment with ¯uoride anion. The hexasubstitution of hexabromobenzene (135) with 134 afforded hexaethynylbenzene (136) after desilylation in total yield of 287. 1). Hexabutadiynylbenzene was prepared similarly [60]. As another method, terminal alkynes 139 are prepared in excellent yields by the coupling of commercially available ethynyl Grignard (138) or ethynylzinc bromide with halides, without protection and deprotection [61].

No cyclization occurs when there is the double bond, instead of the epoxide. The alkynyl iodide 164 undergoes the cross coupling with a terminal alkyne to give the 1,3-diyne 165 [76]. No homocoupling product is formed. This reaction offers a good synthetic route to unsymmetric 1,3-diynes. 2 Reactions of Internal and Terminal Alkynes via Insertion Internal alkynes 166 insert to some Pd±carbon bonds to generate the alkenyl±Pd bonds 167. This process can be regarded as the syn addition of organopalladium species to alkynes, or the carbopalladation of alkynes.

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