ISSN:
0009-2940
Keywords:
1,3-Dithietane 1,1,3,3-tetraoxide, alkylation, silylation of
;
Nonafluorobutanesulfonic acid esters
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Substitution Reactions of 1,3-Dithietane 1,1,3,3-Tetraoxide (Disulfene)Alkylation of 1,3-dithietane 1,1,3,3-tetraoxide (disulfene, 5) with alkyl iodides in the presence of NaH provides a mixture of cis/trans1-isomers 4a-c (Me, Et, iPr), which are further alkylated to 7a, b or brominated to 1a, b. Only by using the respective nonafluorobutanesulfonic acid esters (nonaflates, C4F9SO2OR) silylations, germylation, or stannylation of 5 is achieved with formation of the 2,4-disilyl (6a, b, d, e), -digermyl (3f), and -distannyl (3g) compounds as well as the mixed alkyl/silyl species 2a, b. Attempts to synthesize compounds with a 2,4-bridged structure by treatment of 5 with I-(CH2)3-I/NaH were unsuccessful, but yielded the unusual dispiro disulfene 8, whereas the dicyclic 2,4-bridged compound 9 has been obtained from 5 and the respective 1,2-disilyl ester of ethane. The first example of a 1λ6,3λ6-1,3-dithiete 10 is obtained by tetrasilylation of 5 accompanied by a rearrangement of two of the bulky Et3Si groups to the sulfone groups.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19931260234
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