Cyclopentene 1,6-alkadiene

The redox-photosensitized amination was applied to the amination of simple alkenes and 1,3-alkadienes (8) with NHj (Scheme 6.30) [52]. Photoamination of 2,3-dimethyl-2-bntene (8a) gave the Type 11 aminated products, 32a and 32a. It is noteworthy that photoamination of 8 occurred accompanied by the incorporation of 4-cyanophenyl gronps. In the cases of 2,4-dimethyl-2,4-hexadiene (8b) and 2,4-hexadiene (8c), the aminated compounds (32b-i) in which 1,4-addition of the amino and 4-cyanophenyl groups occurred were obtained in fairly good yields. The similar photoamination of l,2,3,4-tetramethyl-l,3-cyclopentadiene (8d) gave selectively 1-amino-4-(4-cyanophenyl)-l,2,3,4-tetramethyl-2-cyclopentene (32j) in 95%. Similar photoamination can be applied to 2,3-dihydrofuran (8e) and 2,3-dihydropyran (8f). 

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