Methodology for the preparation of C1-monoalkylated 1,2-dihydro C70) derivatives: formation of the "other" regioisomer.
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| Abstract | :  Deprotonation of 1,2-C(70)H(2) with TBAOH, followed by alkylation with methyl bromoacetate, results in formation of a C1-monoalkylated 1,2-dihydro-C(70) 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-C(70)H(2) 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 C(70) with Zn and methyl bromoacetate. | 
| Year of Publication | :  2004 | 
| Journal | :  The Journal of organic chemistry | 
| Volume | :  69 | 
| Issue | :  6 | 
| Number of Pages | :  2178-80 | 
| Date Published | :  2004 | 
| ISSN Number | :  0022-3263 | 
| URL | :  https://doi.org/10.1021/jo030242s | 
| DOI | :  10.1021/jo030242s | 
| Short Title | :  J Org Chem | 
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