Photochemical activation of trimethylsilylmethyl allylic sulfones for intramolecular 4+3 cycloaddition
1993; Elsevier BV; Volume: 34; Issue: 34 Linguagem: Inglês
10.1016/s0040-4039(00)73914-1
ISSN1873-3581
AutoresMichael Harmata, Barry F. Herron,
Tópico(s)Organic Chemistry Cycloaddition Reactions
ResumoIrradiation of allylic sulfones 4–7 results in the formation of 4+3 cycloadducts 8–11. Although the yields are poor, this represents the first apparent photochemical generation of acyclic allylic cations for 4+3 cycloadditions. Mechanistically, this process is interpreted as an electron transfer process to form an internal radical cation/radical anion reactive intermediate. This eliminates p-tolylsulfinate anion to form an allylic cation which undergoes an intramolecular 4+3 cycloaddition.
Referência(s)