Highly Selective Synthesis of Acyclic Tert-Aliphatic Carboxylic Acids from Acyclic Tert-Alcohols Using Sulfuric Acid Supersaturated with Carbon Monoxide

References

• Sam , D. J. 1972 . J. Am. Chem. Soc. , 94 : 4024 and references cited therein. For instance
   Web of Science ®Google Scholar
• Falve , J. 1980 . New Synthesis with Carbon Monoxide , 372 New York : Springer-Verlag . For a review:
   Google Scholar
• Koch , H. and Haaf , W. 1958 . Ann. Chem. , 618 : 251 For instance: product distribution in the carboxylation of 2-methyl-2-butanol [C5-acids, 10, C6-acids, 42, C7-acids, 12, and C11- and higher acids, 36%, respectively]; 1,1-dimethylbutyl formate [C5-and C6-acids, 15, C7-acids, 28, C8- and C9-acids, 14, and C13- and higher acids, 43%, respectively].
   Google Scholar
• Koch , H. and Haaf , W. 1958 . Angew. Chem. , 70 : 311 Pincock, R. E., Grigat, E., and Bartlett, P. D., J. Am. Chem. Soc., 1959, 81, 6332; Peters, J. A. and Bekkum, H. van., Recl. Trav. Chim. Pays Bas, 1971, 90, 65; Beeby, P. J. and Sternhell, S., Aust. J. Chem., 1971, 24, 809; Eckhardt, W., Grob, C. A., and Treffert, W. D., Helv. Chim. Acta, 1972, 55, 2432; Golzke, V., Langhals, H., and Ruchardt, C., Synthesis, 1977, 675. For instance
   Google Scholar
• 2-Methyl-2-propanol and 2,3,3-trimethyl-2-butanol gave the corresponding carboxylic acids in good yield3) since the initially formed carbenium ions derived from these alcohols are difficult to rearrange into other carbenium ions containing different carbon skeletons.
   Google Scholar
• Takahashi , Y. , Yoneda , N. and Nagai , H. 1985 . Chem. Lett. , : 1733
   Google Scholar
• Haaf , W. 1966 . Chem. Ber. , 99 : 1149
   Google Scholar
• The concentration of carbon monoxide in various acid systems can be estimated by the absorption amount of carbon monoxide into the system or the evolution amount of carbon monoxide by efficient stirring, CO mol/1-acid: H2SO4-HCO2H with slow stirring (present work), 1.6 − 3.8 × 10−1 at −5 ∼ 20°C; H2SO4-HCO2H with vigorous stirring, 0.9 × 10−3 at 0°C; Cu(CO)+ 3- H2SO4, 3.8 × 10−1 at 30°C; Cu(CO)+ 4- BF3-H2O, 7.2 × 10−1 at 20°C; HF-SbF5 (HF/SbF5 molar ratio, 1), 4.0 × 10−2 at 20°C.
   Google Scholar
• Souma , Y. and Sano , H. 1973 . Bull Chem. Soc. Jpn. , 46 : 3237
   Google Scholar
• Yoneda , N. , Fukuhara , T. , Takahashi , Y. and Suzuki , A. 1974 . Chem. Lett. , : 607
   Google Scholar
• Moyer , W. W. and Marvel , C. S. 1946 . Org. Synth., Coll. , II : 602 and references cited therein.
   Google Scholar
• Turro , N. J. , Byers , G. W. and Leemakeres , P. A. 1964 . J. Am. Chem. Soc. , 86 : 955
   Google Scholar
• Kell , D. R. and McQuillin , F. J. 1972 . J. Chem. Soc., Perkin I , : 2096
   Google Scholar
• Sniegoski , P. J. 1976 . J. Org. Chem. , 41 : 2058
   Web of Science ®Google Scholar
• Pirozhkov , S. D. , Puzitskii , K. V. , Myshenkova , T. N. , Ryabova , K. G. and Eidus , Ya. T. 1977 . Izv. Akad. Nauk SSSR, Ser. Khim. , : 817 Chem. Abstr., 87, 133952e (1977).
   Google Scholar
• Hites , R. A. and Biemann , K. 1972 . J. Am. Chem. Soc. , 94 : 5772
   Google Scholar
• Creger , P. L. 1967 . J. Am. Chem. Soc. , 89 : 2500
   Google Scholar