Answers are grounded in this paper and cite their sources.
Various functionalized cyclic ethers such as oxiranes, oxetanes, and tetrahydrofurans have been prepared, and the regiochemistry of their ring opening with samarium diiodide and acyl chloride or anhydride has been investigated. Alkyl-substituted oxetane 5 and tetrahydrofurans 1 and 2 show almost no regioselectivity. However, high regioselectivities from the branched cyclic ethers (3, 8, 9, and 10) containing ethereal or hydroxyl moieties have been observed. This is probably the result of the bidentate chelated species between samarium and oxygen.
No takes yet. Share an insight, caveat, or question.
Kwon et al. (2002) studied this question.
Synapse has enriched 10 related papers. Consider them for comparative context: