• Archives of Pharmacal Research
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• v.20 no.6
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• pp.647-651
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• 1997

The 6, 6-dibromopenam 6 was treated with $CH_{3}/MgBr$ and carbaldehyde 5 to afford the 6-bromo-6-(1-hydroxy-1-methyl)penicillanate 7, which was reacted with acetic anhybride to give acetoxy compound 8. The deacetobromination of 8 with zinc and acetic acid gave 6-exomethylenpenams, Z-isomer 9 and E-isomer 10, which were oxidized to sulfones 11 and 12 by m-CPBA. The p-methoxybenzyl compounds were deprotected by $AlCl_{3}$ and neutralized to give the sodium salts 13, 14, and 15.

• Journal of the Korean Chemical Society
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• v.40 no.9
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• pp.615-622
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• 1996

(Benzotriazol-1-yl)arenesulfonylalkanes, 2a, 2b, 3a and 3b, were prepared by lithiation of 1-(benzotriazol-1-yl)arenesulfonylmethanes followed by reaction with alkyl iodides. Very bulky molecules such as 1,1-di(benzotriazol-1-yl)-1-aryl-1-thiophenoxymethanes 5, 1,1-di(benzotriazol-1-yl)-1-thiophenoxymethane 9a and 1,1-di(benzotriazol-1-yl)-1,1-dithiophenoxymethane 9b were synthesized. 1,1-Di(benzotriazol-1-yl)-1-benzenesulfoxymethane 10a and 1,1-di(benzotriazol-1-yl)-1-benzenesulfonylmethane 10b were also synthesized by the oxidation of compound 9a, while oxidation of sulfide group on compound 5 and 9b by m-CPBA were not successful. On the other hand, pyrolysis and hydrolysis of 3-(benzotriazol-1-yl)-3-toluenesulfonylpentane 3b gave 3-toluenesulfonyl-2-pentene 11 and diethyl ketone 13a, respectively, which means there are both C-N and C-S bond cleavages.