One-pot synthesis of diarylalkylcarbinols and substituted derivatives through carbon monoxide insertion reactions into aryllithiums
The carbonylation of a THF solution of aryllithium (aryl = Ph, o-anisyl) in the presence of an alkyl bromide, RBr; at atmospheric pressure and -78°C, affords diarylalkylcarbinols in good yields. Alkyl chlorides do not react under similar experimental conditions. This feature makes the reaction parti...
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1987
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| LEADER | 06474caa a22007097a 4500 | ||
|---|---|---|---|
| 001 | PAPER-18064 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518204925.0 | ||
| 008 | 190411s1987 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-0002926130 | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a JORCA | ||
| 100 | 1 | |a Vitale, A.A. | |
| 245 | 1 | 0 | |a One-pot synthesis of diarylalkylcarbinols and substituted derivatives through carbon monoxide insertion reactions into aryllithiums |
| 260 | |c 1987 | ||
| 270 | 1 | 0 | |m Vitale, A.A.; Departamento Química Orgánica, Facultad de Ciencias Exactas, Universidad de Buenos Aires, Pab. II, P. 3 Ciudad Universitaria, 1428 Buenos Aires, Argentina |
| 506 | |2 openaire |e Política editorial | ||
| 504 | |a Narayana, Periasamy, Organic Synthesis via Carbonylation of Organometallic Reagents with Carbon Monoxide (1985) Synthesis, p. 253 | ||
| 504 | |a Seyferth, Weinstein, Wei-lang, Hui, Archer, Direct Nucleophilic Acylation with Acyllithium Reagents: Acyl Anion Synthons Unmasked (1984) Israel Journal of Chemistry, 24, p. 167 | ||
| 504 | |a Lever, (1976) Tetrahedron, 32, p. 1943 | ||
| 504 | |a Chandrasekhar, Andrade, Schleyer, (1981) J. Am. Chem. Soc., 103, p. 5612 | ||
| 504 | |a Seyferth, Hui, (1985) J. Am. Chem. Soc., 107, p. 4551 | ||
| 504 | |a Seyferth, Hui, (1985) J. Org. Chem., 50, p. 1985 | ||
| 504 | |a Nudelman, Vitale, (1981) J. Org. Chem., 46, p. 4625 | ||
| 504 | |a Vitale, Pérez, Outumuro, Nudelman, (1982) Anales Asoc. Quím. Arg., 70, p. 155 | ||
| 504 | |a Barrett, Wilkinson, (1954) Chem. Abstr., 48, p. 2112e. , British Patent 683 950 | ||
| 504 | |a Fleming, (1977) Chem. Abstr., 87, p. 84839. , U.S. Patent 4 031 101 | ||
| 504 | |a A total yield of 30% of 6 is obtained by the succesive conversion of 5 to the cyano derivative [11] and to the ethyl γ-chlorobutyrate [12] and its subsequent reaction with PhLi [8]; Allen, (1941) Organic Synthesis, Collective, 1, p. 156. , Wiley, New York | ||
| 504 | |a Fehnel, (1952) J. Am. Chem. Soc., 74, p. 1569 | ||
| 504 | |a Hamaguchi, (1963) Yakagaku Zasshi, 82, p. 1088. , Chem. Abstr. 87 1977 84839 | ||
| 504 | |a Nudelman, Vitale, (1983) J. Organomet. Chem., 241, p. 143 | ||
| 504 | |a Trzupek, Newirth, Kelly, Nudelman, Whitesides, (1973) J. Am. Chem. Soc., 95, p. 8118 | ||
| 504 | |a Hope, Power, Isolation and crystal structures of the halide-free and halide-rich phenyllithium etherate complexes [(PhLi.Et2O)4] and [(PhLi.Et2O)3.LiBr] (1983) Journal of the American Chemical Society, 105, p. 5321 | ||
| 504 | |a Wittig, Meyer, Lange, Über das Verhalten von Diphenylmetallen als Komplexbildner (1951) Justus Liebigs Annalen der Chemie, 571, p. 167 | ||
| 504 | |a Talaleva, Rodinov, Kocheskov, (1964) Dokl. Chem. (Engl. Transl.), 154, p. 47 | ||
| 504 | |a West, Waack, (1967) J. Am. Chem. Soc., 89, p. 4395 | ||
| 504 | |a West, MTP International Reviews of Science (1972) Inorg. Chem., Ser. One, 4 B, p. 1. , J. Asylett, University Park Press, Baltimore, and ref. therein | ||
| 504 | |a Jackman, Scartmoutzos, (1984) J. Am. Chem. Soc., 106, p. 4627 | ||
| 504 | |a Seebach, Hassig, Gabriel, 13C-NMR.-Spektroskopie von Organolithiumverbindungen bei tiefen Temperaturen. Strukturinformation aus der13C,6Li-Kopplung (1983) Helvetica Chimica Acta, 66, p. 308 | ||
| 504 | |a Brandon, Closs, Hutichinson, (1962) J. Chem. Phys., 37, p. 1878 | ||
| 504 | |a Murray, Trozzolo, Wasserman, Yager, (1962) J. Am. Chem. Soc., 84, p. 3213 | ||
| 504 | |a Fagan, Manriquez, Volmer, Day, Marks, (1981) J. Am. Chem. Soc., 103, p. 2206 | ||
| 504 | |a Fagan, Manriquez, Marks, Day, Vollmer, Day, (1980) J. Am. Chem. Soc., 102, p. 5393 | ||
| 504 | |a Nudelman, Vitale, A CONVENIENT PREPARATION OF α,α-DIPHENYLACETOPHENONE (1981) Organic Preparations and Procedures International, 13, p. 144 | ||
| 504 | |a Shriver, (1969) The Manipulation of Air-Sensitive Compounds, , McGraw-Hill, New york, Ch. 7 | ||
| 504 | |a Bakassian, Descotes, Sinov, (1970) Bull. Soc. Chim. Fr., p. 1084 | ||
| 504 | |a Biernack, Gdula, (1981) Pol. J. Chem., 55, p. 849. , Chem. Abstr. 97 1982 55246e | ||
| 520 | 3 | |a The carbonylation of a THF solution of aryllithium (aryl = Ph, o-anisyl) in the presence of an alkyl bromide, RBr; at atmospheric pressure and -78°C, affords diarylalkylcarbinols in good yields. Alkyl chlorides do not react under similar experimental conditions. This feature makes the reaction particularly useful for the synthesis of alcohols functionalized in the alkyl chain through subsequent reactions of the diaryl(chloro)alkylcarbinols. The procedure can also be adapted to afford substituted cyclic ethers. If the reaction is carried out in the presence of dibromoalkanes, only one bromine atom reacts, affording diaryl(bromo)alkylcarbinols which are useful synthetic intermediates. With secondary and tertiary alkyl bromides diaryl alkyl ethers are obtained in variable yields. © 1987. |l eng | |
| 536 | |a Detalles de la financiación: National Council for Scientific Research | ||
| 536 | |a Detalles de la financiación: Consejo Nacional de Investigaciones Científicas y Técnicas | ||
| 536 | |a Detalles de la financiación: We are indebted to the National Research Council of Argentina (CONICET) to the Science and Technology Secretariat (SECYT) for financial support. F.D. grateful recipient of a CONICET fellowship. UMYMFOR (FCEN-CONICET) acknowledged for the spectroscopic determinations. | ||
| 593 | |a Departamento Química Orgánica, Facultad de Ciencias Exactas, Universidad de Buenos Aires, Pab. II, P. 3 Ciudad Universitaria, 1428 Buenos Aires, Argentina | ||
| 700 | 1 | |a Doctorovich, F. | |
| 700 | 1 | |a Sbarbati Nudelman, N. | |
| 773 | 0 | |d 1987 |g v. 332 |h pp. 9-18 |k n. 1-2 |p J. Organomet. Chem. |x 0022328X |w (AR-BaUEN)CENRE-24 |t Journal of Organometallic Chemistry | |
| 856 | 4 | 1 | |u https://www.scopus.com/inward/record.uri?eid=2-s2.0-0002926130&doi=10.1016%2f0022-328X%2887%2985117-3&partnerID=40&md5=d4ecf0db7dda0126e51c5c132ff5cb6e |y Registro en Scopus |
| 856 | 4 | 0 | |u https://doi.org/10.1016/0022-328X(87)85117-3 |y DOI |
| 856 | 4 | 0 | |u https://hdl.handle.net/20.500.12110/paper_0022328X_v332_n1-2_p9_Vitale |y Handle |
| 856 | 4 | 0 | |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0022328X_v332_n1-2_p9_Vitale |y Registro en la Biblioteca Digital |
| 961 | |a paper_0022328X_v332_n1-2_p9_Vitale |b paper |c PE | ||
| 962 | |a info:eu-repo/semantics/article |a info:ar-repo/semantics/artículo |b info:eu-repo/semantics/publishedVersion | ||
| 999 | |c 79017 | ||