167865-74-9Relevant academic research and scientific papers
Generation, Stability, and Utility of Lithium 4,4′-Di-tert-butylbiphenylide (LiDBB)
Hill, Richard R.,Rychnovsky, Scott D.
, p. 10707 - 10714 (2016)
Several procedures were evaluated for the preparation of lithium 4,4′-di-tert-butylbiphenylide (LiDBB, Freeman's reagent) from lithium metal and 4,4′-di-tert-butylbiphenyl (DBB) in THF. Solutions with nominal concentration of 0.4 and 1.0 M were formed. The stability of LiDBB solutions was evaluated over time, and the gradual uptake of lithium metal was observed. At 0 °C the LiDBB solutions were stable for over a week in THF. At 20 °C the LiDBB solution underwent various decomposition pathways, which led to uptake of more lithium metal and the accumulation of side products. These decomposition pathways were studied, and the importance of ethene in the destruction of THF by LiDBB was observed. On a practical note, LiDBB solutions in THF were stable and effective for over a week at 0 °C or for more than 37 weeks when stored under argon at -25 °C. These observations will extend the utility of LiDBB as a reagent in organic synthesis.
Synthesis of formylsilanes through oxidative cleavage of α-silyl glycols
Von Wachenfeldt, Henrik,Strand, Daniel
, p. 12268 - 12273 (2014/01/06)
A convenient method for the synthesis and isolation of highly reactive formylsilanes by oxidative cleavage of α-silyl glycols is presented. The mild conditions provide an entry to acid- and heat-sensitive members of this theoretically intriguing class of compounds. The utility of the method is demonstrated through the isolation and subsequent diastereoselective derivatization of t-BuMe2- and t-BuPh2-formylsilanes, previously not reported in isolated form.
Synthesis of vinylsilanes by silyl-cupration of acetylenes using tert-butyldiphenylsilyl-cuprate reagents
Barbero, Asuncion,Cuadrado, Purificacion,Fleming, Ian,Gonzalez, Ana M.,Pulido, Francisco,Sanchez, Alicia
, p. 1525 - 1532 (2007/10/02)
The tert-butyldiphenylsilyl-cuprate 2 reacts with acetylenes 1 and 5-10 to give vinyl-cuprates 3 and 11, which react with electrophiles to give the vinylsilanes 4 and 12-17 carrying the relatively hindered and hence unreactive tert-butyldiphenylsilyl group.In comparative tests, the tert-butyldiphenylsilyl group shows some properties that are usefully different from those of relatively unhindered silyl groups and others that are similar.
