Abstract
The singlet oxygen ( 1Δ g) photooxidations of angelic acid salt ( 1 ), tiglic acid salt ( 2 ), 2,3-dimethyl-2-butenoic acid salt ( 3 ), 3-ethoxycarbonyl-5,6-dihydro-2-methyl-4 H-pyrane acid salt ( 4 ), cis-3-hexenoic acid salt ( 5 ), and trans-3-hexenoic acid salt ( 6 ) were conducted in deuterated water. The major and minor ene allylic hydroperoxide products were quantified and indicate that the allylic hydrogen geminal to the carboxylate group is preferentially abstracted in 1– 4 , whereas the allylic hydrogen α to the carboxylate is slightly favored for 5 and 6 . We have attributed the observed regiochemistry in 1– 4 to stabilizing hydrogen bonding interactions between the solvent and the perepoxide, which leads to the major ene product.
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
