1981
DOI: 10.1002/cber.19811140612
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2‐Methyl‐1‐phenyl‐1‐propenyllithium. Ein katalytisch ummetallierbares Vinyllithiumderivat

Abstract: Die rasche und vollstnndige Umwandlung der Vinyllithiurn-Verbindung 1 in die Allyllithium-Verbindung 7 wird 'H-NMR-spektroskopisch verfolgt und durch chemische Umsetzungen belegt. Diese scheinbare Umlagerungsreaktion erfolgt unter katalytischer Mitwirkung des 2-Methyl-lphenyl-1-propens (2). Aus den Reaktionsordnungen, Aktivierungsparametern und der Solvensabhangigkeit wird auf einen intermolekularen Ummetallierungsmechanismus mit deaggregierten und ionisierten Zwischenstufen geschlossen. >Methyl-1-phenyl-1-pro… Show more

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Cited by 30 publications
(18 citation statements)
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“… Compound 4 [( E )/( Z ) = 9:8] was also observed. The 1 H NMR spectroscopic data of the ( E ) isomer were in good agreement with those reported before …”
Section: Resultssupporting
confidence: 90%
See 1 more Smart Citation
“… Compound 4 [( E )/( Z ) = 9:8] was also observed. The 1 H NMR spectroscopic data of the ( E ) isomer were in good agreement with those reported before …”
Section: Resultssupporting
confidence: 90%
“…The HWE reaction of ketone 2b in the presence of DBU (1,8‐diazabicyclo[5.4.0]undec‐7‐ene) and CsCO 3 resulted only in a low yield of the desired product 3b . Instead, compound 4 , where the double bond had migrated into conjugation with the phenyl ring was formed as the major product. Changing the base to NaH, however, allowed the desired α,β‐unsaturated ester 3b to be isolated in 93 % yield.…”
Section: Resultsmentioning
confidence: 99%
“…This procedure was followed by transesterification to the ethyl ester 11, obtained by PAD reduction of diol 4, as shown in Scheme 1. A standard of this material was obtained by carbonylation 11, 15 of the vinyl bromide moiety in 12, whose absolute configuration is securely established. 1,5f The diols derived from allyl and propargyl benzoates, 9 and 10, were reduced with excess PAD, with concomitant saturation of the allyl and propargyl functionalities, and matched with 13, whose absolute configuration had been ascertained by its conversion to the ethyl ester 11 (Scheme 2).…”
Section: Resultsmentioning
confidence: 99%
“…(28 mg, 70%), colorless oil. R f 0.60 (1:1 hexanes/ethyl acetate); [a] D 20 -71.56 (c 0.93, CHCl 3 ); IR (film): n 2976, 2954, 2938, 1750, 1734, 1732, 14337, 1372, 11240, 1221, 1195 cm -1 ; 1 H NMR (600 MHz, CDCl 3 ) d 5.40 (m, 1H), 4.93 (dd, J = 7.9, J = 2.6 Hz, 1H), 4.69 (t, J = 4.9 Hz, 1H), 4.23 (dd, J = 8.0, J = 5.0 Hz, 1H), 3.78 (s, 3H), 3.13 (dt, J = 12.8, J = 4.5 Hz, 1H), 2.21 (dt, J = 14.9, J = 12.9 Hz, 1H), 2.12-2.06 (m, 4H), 1.52 (s, 3H), 1.38 (s, 3H) ppm; 13 C NMR (150 MHz, CDCl 3 ) d 171.4, 170.3, 169.7, 109.9, 75.5, 73.9, 7.1, 68.7, 52.2, 38.11, 27.9, 26.2, 24.9, 20.9 ppm; MS (EI) m/z (%): 313 (M + -CH 3 , 13), 241 (15), 171 (23), 153(47), 43(100); HRMS (M + -CH 3 ) calcd for C 14 H 19 O 8 315.1080, found 315.1082.…”
Section: 7-diacetoxy-22-dimethyl-hexahydro-benzo[13]dioxole-4-carboxy...mentioning
confidence: 99%
“…(1-Phenyl-2,2-dimethylvinyl)lithium, [15] (1,2-diphenylvinyl)lithium, [16] (1,4-diphenyl-1,3-butadienyl)lithium, [17] (2,2-diphenylvinyl)lithium, [18] and (1-phenylvinyl)lithium [19] were prepared according to literature.…”
Section: Experimental Partmentioning
confidence: 99%