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Doubly Metalated Methanol—A Nucleophilic Hydroxymethylation Reagent

1976; Wiley; Volume: 15; Issue: 7 Linguagem: Inglês

10.1002/anie.197604381

1521-3773

Dieter Seebàch, Norbert Meyer,

Catalytic Cross-Coupling Reactions

Angewandte Chemie International Edition in EnglishVolume 15, Issue 7 p. 438-438 Communication Doubly Metalated Methanol—A Nucleophilic Hydroxymethylation Reagent† Prof. Dr. Dieter Seebach, Prof. Dr. Dieter Seebach Institut für Organische Chemie der Universität, Heinrich-Buff-Ring 58, 6300 Giessen (Germany)Search for more papers by this authorDipl.-Chem. Norbert Meyer, Corresponding Author Dipl.-Chem. Norbert Meyer Institut für Organische Chemie der Universität, Heinrich-Buff-Ring 58, 6300 Giessen (Germany)Institut für Organische Chemie der Universität, Heinrich-Buff-Ring 58, 6300 Giessen (Germany)Search for more papers by this author Prof. Dr. Dieter Seebach, Prof. Dr. Dieter Seebach Institut für Organische Chemie der Universität, Heinrich-Buff-Ring 58, 6300 Giessen (Germany)Search for more papers by this authorDipl.-Chem. Norbert Meyer, Corresponding Author Dipl.-Chem. Norbert Meyer Institut für Organische Chemie der Universität, Heinrich-Buff-Ring 58, 6300 Giessen (Germany)Institut für Organische Chemie der Universität, Heinrich-Buff-Ring 58, 6300 Giessen (Germany)Search for more papers by this author First published: July 1976 https://doi.org/10.1002/anie.197604381Citations: 20 † Part of projected thesis of N. Meyer, Universität Giessen. N. M. thanks the Studienstiftung des Deutschen Volkes for a grant.—This work was supported by the Fonds der Chemischen Industrie. We are grateful to the Schering company, Bergkamen, for a gift of tributyltin chloride. AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat No abstract is available for this article. References 1 See, e.g., the Prins reaction: J. Mathieu and J. Weill-Raynal: Formation of C—C Bonds. Thieme. Stuttgart 1973, Vol. 1. references cited on pp. 18–33. 2 J. C. Lahournère and J. Valade, C. R. Acad. Sci. C 270, 2080 (1970). 3 It is already known that alkoxymethyllithium ( U. Schöllkopf in Houben-Weyl-Müller: Methoden der Organischen Chemie. Thieme. Stuttgart 1970, Vol. 13/1, p. 133) and dialkylaminomethyllithium compounds [ D. J. Peterson and J. F. Ward, J. Organomet. Chem. 66, 209 (1974), references cited therein] can be prepared by Sn/Li exchange. 4 Cf. also doubly metalated thiols: D. Seebach and K. H. Geiss. Angew. Chem. 86, 202 (1974); Angew. Chem. Int. Ed. Engl. 13, 202 (1974); K. H. Geiss, B. Seuring, R. Pieter, and D. Seebach, Angew. Chem. Int. Ed. Engl. 86, 484 (1974) and Angew. Chem. Int. Ed. Engl. 13, 479 (1974), respectively; D. Seebach, K. H. Geiss, and M. Pohmakotr, Angew. Chem. Int. Ed. Engl. 88, 449 (1976) and Angew. Chem. Int. Ed. Engl. 15, 437 (1976), respectively. 5 According to D. O. DePree and J. D. Johnston, US-Pat. 3239568: Chem. Abstr. 64, 15921e (1966), double metalations are feasible under extreme conditions. We were unable to obtain a reagent of type (3) by reaction of formaldehyde with alkali metals. The high solubility of our reagent in pentane, even at −78°C, indicates that (3) is somehow “complexed” with the R4Sn present in the solution! 6 Hydroxymethylation of an alkyl halide has been performed with LiCH2BR2 [M. W. Rathke and R. Kow, J. Am. Chem. Soc. 94, 6854 (1972)]. Citing Literature Volume15, Issue7July 1976Pages 438-438 ReferencesRelatedInformation