Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 19, Pages 8759-8769Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b01219
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Funding
- Conseil Regional de Bourgogne [PART-IIVIE SMT08]
- CNRS
- Universite de Bourgogne (Nano diamonds Functionalization and Metallization project) [3MIM-P4]
- United States Department of Energy, Office of Science, Basic Energy Sciences, Materials Sciences and Engineering Division [DE-AC02-76SF00515]
- Ukrainian Basic Research Foundation, Ministry of Science and Education of Ukraine
- Alexander-von-Humboldt Foundation
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Direct unequal C-H bond difunctionalization of phosphorylated diamantane was achieved in high yield from the corresponding phosphonates. Reduction of the functionalized phosphonates provides access to novel primary and secondary alkyl/aryl diamantane phosphines. The prepared primary diamantyl phosphines are quite air stable compared to their adamantyl and especially alkyl or aryl analogues. This finding is corroborated by comparing the singly occupied molecular orbital energy levels of the corresponding phosphine radical cations obtained by density functional theory computations.
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