Tetrahedron p. 1041 - 1052 (1998)
Update date:2022-08-29
Topics:
Jou, Der-Ching
Hsiao, Tsung-Yu
Wu, Ming-Yuan
Kong, Kwang-Cheng
Cheng, Chien-Hong
2,3-Dimethyl-1,3-butadiene and cyclic dienes react with β-iodoenones (RI: 3-Iodo-2-cyclohexen-1-one, 5,5-dimethyl-3-iodo-2-cyclohexen-1-one and 3-iodo-2-cyclopenten-1-one) in the presence of Zn and catalytic amount of NiBr2 to afford the corresponding homo 1,4-addition products in good yields. For 2,3-dimethyl-1,3-butadiene, only the products RCH2C(CH3)=C(CH3)CH2R with Z geometry were observed. For cyclic dienes, the products observed are RCHCH=CHCHR(CH2)(n)CH2 in which the two alkenyl substituents R are cis to each other.
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