2-BUTENE, 1-IODO-4-PHENYL

C. (E)- -Iodo-4 -phenyl-2-butene. In a 20-ml., round-bottomed flask are placed 2.0 g. (0.008 mole) of 2-(4/-phenyl-l -buten-3 -yl)thio-2-thiazoline, 5 ml. of methyl iodide [Methane, iodo-], and 2 ml. of di-methylformamidc. The resulting solution is heated at 75-80° for 2.5 hours under a nitrogen atmosphere (Note 13), cooled, and poured into 10 ml. of water. Extraction with three 12-ml. portions of ether separates the product from water-soluble by-products. The extracts are combined, washed with 8 ml. of 1% aqueous sodium thiosulfate and two 8-ml. portions of water, dried over anhydrous magnesium sulfate, and filtered to remove the drying agent. Removal of ether by distillation at 30° (100 mm.) leaves 1.5-1.7g. (74-82%) of ( )-l-iodo-4-phenyl-2-butene (Notes 14 and 15). 

A)-l-Iodo-4-phenyl-2-butene has been prepared previously by addition of C6H5 and Cl units (generated by decomposition of C6H5N2C1 in the presence of a catalytic amount of CuCl2) across the conjugated system of butadiene, followed by treatment with ethanolic potassium iodide solution.3... 

Ethoxy-l-iodo-3-butene, 2449 Hexamethylenetetramine tetraiodide, 2471 (Hydroxy)(oxo)(phenyl)-A3-iodanium perchlorate, 2299 Iodinated poly(sulfur nitride), 4622... 

This methodology was also applied to Negishi coupling. When 1-fluoro-l-iodo-4-phenyl-l-butene 42b (E Z = 78 22) was subjected to the reaction with an alkyl... 

The hydroalumination of terminal alkenes and dienes using BujAl as aluminum source can also be catalyzed by late transition metal complexes such as (PPh3)2PdCl2 [38]. The reactions are carried out at room temperature, the use of dichloromethane as a solvent is crucial because it probably regenerates the catalytically active Pd(II) species by reoxidizing Pd(0) complexes formed in side reactions. Internal C=C bonds are not hydroaluminated under these conditions. Functional groups such as Cl, Br, and PhS in a position remote to the terminal C=C bond are tolerated, however, certain substrates such as 4-bromo-l-butene, 11-iodo-l-undecene, allyl phenyl ether, allyl benzyl ether, and (3 )-l,3-decadiene did not provide the desired hydroa-... 

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