ISSN:
0009-2940
Keywords:
Electrophilic aromatic substitution
;
Electrophilic vinylic substitution
;
Aromatic aldehydes
;
α,β-Unsaturated aldehydes
;
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 (7a-m), heteroaromatic (7n-r), and α,β-unsaturated aldehydes (8a-f) is described. The reaction of trialkylaryl- (2a-o), heteroaryl- (2p-t), and 1-alkenylstannanes (4a-f and 5a-f) with dichloromethyl methyl ether (1, DCME) in the presence of aluminium trichloride followed by hydrolysis provides the corresponding aldehydes. In the case of arylstannanes the ipso-isomers are generally formed; the p-alde-hydes occur as side products. The electrophilic substitution of 1-alkenylstannanes with 1 leads to α,β-unsaturated aldehydes in an ipso- and stereospecific manner. A comparison of the leaving abilities of the stannyl and silyl groups shows a lower or even zero reactivity of the silyl-substituted compounds 6a-c towards the electrophile 1. In the silylstannylal-kene 6c only the stannyl group reacts whereas the stannyl function remains unaffected in the product, aldehyde 11.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19961290111
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