Journal
ORGANIC LETTERS
Volume 19, Issue 17, Pages 4504-4507Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b02064
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Funding
- National Science Foundation [CHE-1361104]
- National Science Foundation through XSEDE Science Gateways Program [TG-CHE040013N]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1361104] Funding Source: National Science Foundation
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Additions of amines or thiols to 7-oxanorbornadienes promote retro-[4 + 2] reactions to yield furans. Substitution at the bridgehead position also greatly influences the stability of the oxanorbornene adducts. Activation and reaction energies were computed with the M06-2X density functional, the origins of amine and thiol promoted fragmentation, and how substituent effects control fragmentation rates and reaction energetics are reported.
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