Self-protection: The advantage of radical oligomeric mixtures in organic synthesis

Atom-transfer radical oligomers of allyl iodoacetates were converted to 4-pentenoic acids upon treatment with zinc. Reactions of the radical oligomers of various omega-alkenyl iodoacetates with Grignard reagents afforded the corresponding substituted tetrahydrofuran derivatives. These results indicated that radical oligomeric mixtures not only serve as versatile intermediates in organic synthesis, but also exhibit unique advantages in that the oligomeric mixtures are self-protected and the deoligomerization functions as the simultaneous deprotection.