ISSN:
0009-2940
Keywords:
Zwitterions, heteroaromatic
;
Lone electron pair density, role in alkylations
;
Calculations, AM1
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The alkylation of the two differently fused tricyclic zwitterions 3 and 5 was compared. The linear system 3 was converted into the N-methyl salt 4 on treatment with dimethyl sulfate and into the O-methyl product 12 on treatment with Meerwein's reagent. The angular system 5, in turn, was predominantly transformed into the O-methyl product 14. Theoretical considerations on modified FMO treatment taking into account the lone-pair densities (cn-HOMO) suggested that linear 3 was methylated only at the oxygen position (affording 12) and 4 is a thermodynamically controlled remethylation product. A critical interpretation of cn-HOMO vs. c-HOMO is discussed.
Additional Material:
2 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19921250426
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