4370-78-9Relevant articles and documents
Reductive Lithiation of Sulfur-containing Heterocycles With Aromatic Radical Anions: Synthetic Applications
Florio, Saverio,Capriati, Vito,Gallo, Antonio,Cohen, Theodore,Chen, Fangping,Kulinski, Tomasz
, p. 351 - 358 (2007/10/03)
2H-3,4-dihydro-1-benzothiopyran, 1, and 2,3-dihydrobenzothiophene, 8, have been redctively cleaved by lithium 4,4'-di-tert-butylbiphenylide (LDBB) to the anions 2 and 9, respectively.The dianion 2 can be captured with MeOD to give the deuteriated compound 3 and with carbonyl compounds to give the hydroxyalkylbenzenethiols 4a-e, which in turn have been cyclized to the tetrahydrobenzothiepins 5a-e.Similarly, the dianion 9 reacts with MeOD furnishing 10 and with carbonyl compounds yielding the hydroxyalkylbenzenethiols 11.Benzenethiol 11a has beeen cyclized to the thiochromane 12.The reductive lithiation of 2,2,3-trimethylbenzothiazoline, 13, generates the"unstabilized' α-amino tertiary carbanion 14, which has been trapped with a number of electrophiles to give the products 15, 16, 19, 20 and 23-25.
4-amino-2,3,4,5-tetrahydro-1-benzoxepin-5-ols, 4-amino-2,3,4,5-tetrahydro-1-benzothiepin-5-ols, and related compounds.
Huckle,Lockhart,Webb
, p. 2252 - 2260 (2007/10/05)
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