Methodology for the preparation of C1-monoalkylated 1,2-dihydro C70) derivatives: formation of the "other" regioisomer.
Author | |
---|---|
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
|
Download citation |