Dichotomous Reactivity of PCl₅ and PBr₅ Toward Cyclic Ketones: A One-Step Preparation of 1,1,2-Trichlorocycloalkanes

References

• Jacobs , T. L. 1949 . Org. React. (N.Y.) , 5 : 1
   Google Scholar
• Fridland , S. V. and Chernokal'skii , B. D. 1978 . Russ. Chem. Rev. , 47 : 742
   Google Scholar
• Hudrlik , P. F. and Kulkarni , A. K. 1983 . Tetrahedron , 41 : 1179 Reviews and leading references:
   Google Scholar
• McCullough , R. D. and Cowan , D. O. 1985 . J. Org. Chem. , 50 : 4646
   Web of Science ®Google Scholar
• Lambert , J. B. , Wang , G. , Finzel , R. B. and Teramura , D. H. 1987 . J. Am. Chem. Soc. , 109 : 7838 Recent examples
   Google Scholar
• Brown , A. B. , Chronister , C. W. , Watkins , D. M. , Mazzaccaro , R. J. , Rajski , S. R. and Fountain , M. G. 1991 . Annual Meeting of the Florida Section, American Chemical Society; Abstract , : 28 Presentations
   Google Scholar
• Brown , A. B. , Chronister , C. W. , Watkins , D. M. , Mazzaccaro , R. J. , Rajski , S. R. and Fountain , M. G. 1991 . Abstract ORGN . Fourth Chemical Congress of North America , : 263
   Google Scholar
• Vysotskii , V. I. , Kalinov , S. M. and Prokopenko , V. V. Far Eastern State University . U.S.S.R. Patent 1 551 709 . 1990 . After completion of this work, conversion of 1b and 1c to 2b and 2c respectively, by neat PCl5 at 105–120[ddot], was described in a patent; our conditions are milder than these.
   Google Scholar
• 1990 . Chem. Abstr. , 113 : 131619h
   Google Scholar
• Tishchenko , D. V. 1938 . Zh. Obshch. Khim. , 8 : 1326
   Google Scholar
• 1939 . Chem. Abstr. , 33 : 41906
   Google Scholar
• Mousseron , M. and Jacquier , R. 1950 . Bull. Soc. Chim. Fr. , : 648
   Google Scholar
• Mousseron , M. , Jacquier , R. , Henry , R. and Mousseron-Canet , M. 1953 . Ibid. , : 628
   Google Scholar
• Lazukina , L. A. , Kolodyazhnyi , O. I. , Pesotskaya , G. V. and Kukhar' , V. P. 1931, 1976 . J. Gen. Chem. USSR , 46
   Google Scholar
• Wolinsky , J. , Thorstenson , J. H. and Killinger , T. A. 1978 . J. Org. Chem. , 43 : 875
   Web of Science ®Google Scholar
• Hoffmann , H. M. R. and Vinter , J. G. 1974 . J. Org. Chem. , 39 : 3921
   Google Scholar
• Sato , K. , Inoue , S. , Kuranami , S. and Ohashi , M. 1977 . J. Chem. Soc., Perkin Trans. , 1 : 1666
   Google Scholar
• Folkins , P. L. and Harpp , D. N. 1992 . J. Org. Chem. , 57 : 2013
   Google Scholar
• Freeman , R. and McIntyre , L. 1992 . Isr. J. Chem. , 32 : 231 A recent discussion
   Google Scholar
• Bax , A. and Subramanian , S. 1986 . J. Magn. Reson. , 67 : 565
   Web of Science ®Google Scholar
• Garbisch , E. W. Jr. 1964 . J. Am. Chem. Soc. , 86 : 1780 1H:
   Google Scholar
• Pan , Y.-H. and Stothers , J. B. 1967 . Can. J. Chem. , 45 : 2943
   Google Scholar
• Olieman , C. , Maat , L. and Beyerman , H. C. 1978 . Recl. Trav. Chim. Pays-Bas , 97 : 31 1 3C
   Google Scholar
• Blomquist , A. T. , Liu , L. H. and Bohrer , J. C. 1952 . J. Am. Chem. SoC. , 74 : 3643
   Google Scholar
• Posplsek , J. , Vesely , Z. and Trojanek , J. 1968 . Collect. Czech. Chem. Commun. , 33 : 76
   Google Scholar
• Gilbert , J. C. and Baze , M. E. 1984 . J. Am. Chem. Soc. , 106 : 1885
   Google Scholar
• Newman , M. S. , Fraenkel , G. and Kirn , W. N. 1963 . J. Org. Chem. , 28 : 1851
   Web of Science ®Google Scholar
• McClelland , B. W. , Hedberg , L. and Hedberg , K. 1983 . J. Mol. Struct. , 99 : 309 and references cited
   Web of Science ®Google Scholar
• Spiegler , L. and Tinker , J. M. 1939 . J. Am. Chem. Soc. , 61 : 940
   Google Scholar
• Kosolapoff , G. M. and Huber , W. F. 1946 . Ibid. , 68 : 2540
   Google Scholar
• Uemura , S. , Okazaki , H. , Osoe , A. and Okano , M. 1978 . Bull. Chem. Soc. Jpn. , 51 : 3568
   Google Scholar
• Timokhin , B. V. , Dmitriev , V. K. , Sergienko , L. M. , Ratovskii , G. V. and Ivanova , N. A. 1983 . J. Org. Chem. USSR , 19 : 737 and references cited
   Google Scholar
• Finch , A. , Gates , P. N. and Muir , A. S. 1981 . J. Chem. Soc., Chem. Commun. , : 812 and references cited
   Google Scholar
• Keeffe , J. R. , Kresge , A. J. and Schepp , N. P. 1990 . J. Am. Chem. Soc. , 112 : 4862
   Web of Science ®Google Scholar
• Dubois , J.-E. , El-Alaoui , M. and Toullec , J. 1981 . Ibid. , 103 : 5393
   Google Scholar
• Looker , J. J. 1966 . J. Org. Chem. , 31 : 3599
   Google Scholar
• Griesbaum , K. , Kibar , R. and Pfeffer , B. 1974 . Liebigs Ann. Chem. , : 214
   Google Scholar
• McKay , S. E. and Brown , A. B. to be published
   Google Scholar
• Sanders , J. K. M. and Hunter , B. K. 1988 . Modern NMR Spectroscopy , pp. 252 – 257 . Oxford : Oxford University Press . A discussion
   Google Scholar
• Kozima , K. and Suetaka , W. 1961 . J. Chem. Phys. , 35 : 1516
   Google Scholar
• Buys , H. R. , Altona , C. and Havinga , E. 1967 . Recl. Trav. Chim. Pays-Bas , 86 : 1007
   Google Scholar
• Kohler , E. P. , Tishler , M. , Potter , H. and Thompson , H. T. 1939 . J. Am. Chem. Soc. , 61 : 1057
   Google Scholar
• Braude , E. A. , Forbes , W. F. , Gofton , B. F. , Houghton , R. P. and Waight , E. S. 1957 . J. Chem. Soc. , : 4711
   Web of Science ®Google Scholar
• Borsdorf , R. , Flamme , W. , Kumpfert , H. and Mühlstädt , M. 1967 . J. Prakt. Chem. , 307 : 73
   Google Scholar
• The C-1 assignments of trans-4c and 5c may be reversed
   Google Scholar