Abstract
Difluoro-pentafluorosulfanyl-iodomethane (SF5CF2I) was used in Et3B-mediated radical addition reactions toward electronically different types of alkenes. Reactions with different enol ethers were nonselective in heptane as solvent, while butyl vinyl ether reacted selectively with SF5CF2I in dichloromethane to give the SF5CF2-substituted acetaldehyde dibutyl acetal in moderate yield. Reactions with less electron-rich alkenes such as dec‑1-ene, allyl acetate, and vinyl acetate led to the expected 1-(SF5CF2)-2-iodo products with fair yields. The strained dienes (Z,Z)-cycloocta-1,5-diene and norbornadiene did not yield 1,2-addition products but provided either mixtures of the diastereomeric 2-iodo-6-(CF2SF5)-bicyclo[3.3.0]octanes or the corresponding 3,5-disubstituted nortricyclene derivatives, respectively, by intermediate transannular participation of the second double bond.
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