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Organic Synteses vol 70 - Meyers A.I.

Meyers A.I. , Boecman R.K. Organic Synteses vol 70 - John Wiley & Sons, 1992. - 163 p.
ISBN 0-471-57743
Download (direct link): organicsynthesesvol701992.pdf
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2,3,4,5-tetramethylphosphole has been reported by Nief, et at.2 That procedure involved aluminum chloride - coupling of 2-butyne, followed by reaction with dichlorophenylphosphine to form a chlorophospholium tetrachloroaluminate which was then reduced with tributylphosphine to produce the phosphole in 68% yield.
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Using a procedure similar to that described here, or using isolated zirconium metallacycles as reagents, we have been able to prepare not only phospholes, but also arsoles, stiboles, bismoles, siloles, germoles, stannoles, galloles, thiophenes, selenophenes, and borole Diels-Alder dimers.4 Since a number of other titanium and zirconium metallacycles are readily available,4 these reagents should be useful in the preparation of a variety of heterocycles.
1. E. I. du Pont de Nemours and Co., Inc., Central Research and Development Department, Experimental Station, Box 80328, E328/364, Wilmington, DE 19880-0328. Contribution No. 5123. We thank Ronald J. Davis for technical assistance.
2. Nief, F.; Mathey, F.; Ricard, L.; Robert, F. Organometallics 1988, 7, 921.
3. Mathey, F. Chem. Rev. 1988, 88, 429; Mathey, F. Phosphorus Sulfur 1983, 18, 101; Mathey, F.; Fischer, J.; Nelson, J. H. Struct. Bonding (Berlin) 1983, 55, 153; Mathey, F. In "Topics in Phosphorus Chemistry;" Grayson, M.; Griffith, E. J., Eds.; Wiley: New York, 1980; Vol. 10, p. 1-128.
4. Fagan, P. J.; Nugent, W. A. J. Am. Chem. Soc. 1988, 110, 2310; Fagan, P. J.; Bums, E. G.; Calabrese, J. C. J. Am. Chem. Soc. 1988, 110, 2979; RajanBabu, T. V.; Nugent, W. A.; Taber, D. F.; Fagan, Paul, J. J. Am. Chem. Soc. 1988, 110, 7128; Buchwald, S. L.; Watson, B. T.; Lum, R. T.; Nugent, W. A. J. Am. Chem. Soc. 1987, 109, 7137.
5. Negishi, E.-i.; Cederbaum, F. E.; Takahashi, T. Tetrahedron Lett. 1986, 27, 2829.
276
Appendix
Chemical Abstracts Nomenclature (Collective Index Number); (Registry Number)
1-Phenyl-2,3,4,5-tetramethylphosphole: 1H-Phosphole, 2,3,4,5-tetramethyM-phenyl-(12); (112549-07-2)
Zirconocene dichloride: Zirconium, dichloro-7t-cyclopentadienyl- (8); Zirconium, dichlorobis(ri5-2,4-cyclopentadien-1-yl)- (9); (1291-32-3)
2-Butyne (8,9); (503-17-3)
Dichlorophenylphosphine: Phosphonous dichloride, phenyl- (8,9); (644-97-3)
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Unchecked Procedures
Accepted for checking during the period June 1, 1990 through May 1, 1991. An asterisk (*) indicates that the procedure has been subsequently checked.
In accordance with a policy adopted by the Board of Editors, beginning with Volume 50 and further modified subsequently, procedures received by the Secretary and subsequently accepted for checking will be made available upon request to the Secretary, if the request is accompanied by a stamped, self-addressed envelope. (Most manuscripts require 540 postage).
Address requests to:
Professor Jeremiah P. Freeman Organic Syntheses, Inc.
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It should be emphasized that the procedures which are being made available are unedited and have been reproduced just as they were first received from the submitters. There is no assurance that the procedures listed here will ultimately check in the form available, and some of them may be rejected for publication in Organic Syntheses during or after the checking process. For this reason, Organic Syntheses can provide no assurance whatsoever that the procedures will work as described and offers no comment as to what safety hazards may be involved. Consequently, more than usual caution should be employed in following the directions in the procedures.
Organic Syntheses welcomes, on a strictly voluntary basis, comments from persons who attempt to carry out the procedures. For this purpose, a Checker's Report form will be mailed out with each unchecked procedure ordered. Procedures which have been checked by or under the supervision of a member of the Board of Editors will continue to be published in the volumes of Organic Syntheses, as in the past. It is anticipated that many of the procedures in the list will be published (often in revised form) in Organic Syntheses in future volumes.
278
2551R* 2552R* 2571*
2576*
2577*
2578
2579R*
2581*
2583*
2586*
Tributyl (3-methyl-2-butenyl)tin.
Y. Naruta, Y. Nishigaichi, and K. Maruyama, Department of Chemistry, Faculty of Science, Kyoto University, Sakyo-ku, Kyoto 606, Japan
Ubiquinone-1.
Y. Naruta and K. Maruyama, Department of Chemistry, Faculty of Science, Kyoto University, Sakyo-ku, Kyoto 606, Japan
9-Bromo-9-phenylfluorene.
T. F. Jamison, W. D. Lubell, J. M. Dener, M. J. Krische and H. Rapoport, Department of Chemistry, University of California, Berkeley, CA 94720
Benzoannelation of Ketones.
M. A. Tius and G. S. K. Kannangara, Department of Chemistry, The University of Hawaii, Honolulu, Hawaii 96822
3-(1 -Octen-1 -yl)cyclopentanone.
R. C. Sun, M. Okabe, D. L. Coffen, and J. Schwartz, Chemistry Research Department, Hoffmann-La Roche Inc., Nutley, NJ 07110
Asymmetric Hydrogenation of Allylic Alcohols Using BINAP-Ruthenium Complexes: (S)-(-)-Citronellol.
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