Abstract
Deprotonation of 1,2-C70H2 with TBAOH, followed by alkylation with methyl bromoacetate, results in formation of a C1-monoalkylated 1,2-dihydro-C70 derivative. The position of the alkyl group (C1) was established by NMR spectroscopy and comparison with literature spectra of C2-monoalkylated analogs. Presumably, C1-alkylation is the major process due to selective deprotonation of 1,2-C70H2 at C1. Substitution of benzyl bromide for methyl bromoacetate results in rapid dialkylation, unless the amount of base is carefully controlled, in which case C1-monobenzylation is the major process. This methodology for alkylation at C1 is complimentary to methods for the C2-monoalkylation of C70 with Zn and methyl bromoacetate.
Original language | English |
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Pages (from-to) | 2178-2180 |
Number of pages | 3 |
Journal | Journal of Organic Chemistry |
Volume | 69 |
Issue number | 6 |
DOIs | |
State | Published - Mar 19 2004 |
ASJC Scopus subject areas
- Organic Chemistry