Iodophenyl acetylene

STEPHENS CASTRO Acetylene cycloptiane synthesis Polyacetylene cyclophane synthesis from an iodophenyl copper acetylide... 

Unless otherwise stated, all manipulations are carried out under an atmosphere of argon using standard Schlenk techniques.13 The glassware used in the preparation of (2-iodophenyl)acetylene and the Stephens-Castro coupling of copper acetylide is dried in an oven at 140°C overnight. Potassium tm-butoxide (Aldrich)8 is sublimed at 150°C on a diffusion-pump vacuum... 

A mixture of N (2-iodophenyl)methanesulfonamide, phenylacetylene, and catalytic amounts of PdCl2(PPh3)2 and Cut in 2 1 EtjN/DMF heated in a sealed tube at 80° for 24h l-methanesulfonyl-2-phenylindole. Y 66%. The 2-step indole synthesis via N-(o-acetylene)urethans (Chem. Pharm. Bull. 25, 1823 (1987)) was unsuiteble for preparing C2-functionalized derivs. F.e.s. T. Sakamoto et al., Chem. Pharm. Bull 26, 1305-8 (1988). 

TABLE 1. Results (polymer yield, Y, and weight-average molecular weight, Mw) of polymerization of (iodophenyl)acetylenes and p-nitrophenylacetylene with various catalysts... 

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