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.
Read or Download The Chemistry of Amino, Nitroso, Nitro and Related Groups, Supplement F2 Part 2 PDF
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Extra resources for The Chemistry of Amino, Nitroso, Nitro and Related Groups, Supplement F2 Part 2
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 .
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 . 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 .
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 . 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.