2009
DOI: 10.1016/j.jorganchem.2009.05.035
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Lithiated γ-O-functionalized propyl phenyl sulfides and sulfones of the type Li[CH(SOxPh)CH2CH2OR] (x=0, 2). [Li{CH(SPh)CH2CH2Ot-Bu}(tmeda)] – A structurally characterized organolithium inner complex

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Cited by 11 publications
(9 citation statements)
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“…Chelation of lithium in 33 by the methoxy group would generate an unfavorable sulfone gauche interaction. The mechanistic rational is supported by X‐ray crystal structure analysis of a related lithiated sulfone in which a direct Li–C bond and intramolecular Li–O coordination was observed 17,18…”
Section: Resultsmentioning
confidence: 87%
“…Chelation of lithium in 33 by the methoxy group would generate an unfavorable sulfone gauche interaction. The mechanistic rational is supported by X‐ray crystal structure analysis of a related lithiated sulfone in which a direct Li–C bond and intramolecular Li–O coordination was observed 17,18…”
Section: Resultsmentioning
confidence: 87%
“…4. Type II ligands with a C 3 spacer (n ¼ 3) are found to form organorhodium intramolecular coordination compounds (22,23) irrespective of the nature of the sulfur functionalization (x ¼ 0e2) [24,29]. In the case of the sulfinylfunctionalized ligands (x ¼ 1) the deprotonation of the prochiral CH 2 group creates a second chiral center; noteworthy, the formation of the respective organorhodium complexes (22b, 23b) proved to be diastereoselective.…”
Section: Discussionmentioning
confidence: 99%
“…4 Hz, P of dppe trans to Cl). 23.1 (m, 2 J( 31 P, 31 P) ¼ 328. 6 Hz, 2 J( 31 P, 31 P) ¼ 9.0 Hz, 1 J( 103 Rh, 31 P) ¼ 133.…”
Section: Preparation Of [Rhcl{ph 2 P(ch 2 ) N S(o) X Ph-kp}l 2 ] (6e11)mentioning
confidence: 99%
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“…[1] β-and γ-Hydroxy sulfides are important organic intermediates that possess various applications; they have been used in the synthesis of biologically active compounds that show anticancer, anti-HIV, and 5-HT binding properties; [2] they have been used in the synthesis of crown ether ring-fused uridine analogs [3] and aryl vinyl sulfones; [4] they can be used as base protecting groups for thymidine analogs [5] and in the construction of natural products, [6] metallophthalocyanines, [7] organolithium complexes, [8] and α,β-unsaturated lactones. [1] β-and γ-Hydroxy sulfides are important organic intermediates that possess various applications; they have been used in the synthesis of biologically active compounds that show anticancer, anti-HIV, and 5-HT binding properties; [2] they have been used in the synthesis of crown ether ring-fused uridine analogs [3] and aryl vinyl sulfones; [4] they can be used as base protecting groups for thymidine analogs [5] and in the construction of natural products, [6] metallophthalocyanines, [7] organolithium complexes, [8] and α,β-unsaturated lactones.…”
Section: Introductionmentioning
confidence: 99%