ISSN:
0009-2940
Keywords:
Electrophilic aromatic substitution
;
Electrophilic vinylic substitution
;
Trialkylstannanes, application of
;
Arylsulfonates, sodium salts of
;
Vinylsulfonates, sodium salts of
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
A mild and effective method for the preparation of a variety of aromatic, olefinic, and acetylenic sodium sulfonates is described. The reaction of trialkylaryl- (2a-k) and -heteroarylstannanes (4a-d), bis-(1-alkenyl)dibutylstannanes (6a-f), or trialkylalkynylsta manes with trimethylsilyl chlorosulfonate (1) followed by hydrolysis with aqueous NaHCO3 provides the sodium sulfonates in an ipso-specific and in the case of vinylic stannanes stereospecific manner. A comparison of the reactivity of stannylated and silylated olefinic compounds 13 and 14 underlines the greater leaving ability of the stannyl moiety. The in situ preparation of the stannanes makes it possible to apply the synthetic method to natural products such as N-substituted apocodeine (17).
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19951280609
