References
- Bruceantin Support Studies 4. For paper #3 see R. J. Pariza, P. L. Fuchs, in press
- Kato , M. , Heima , K. , Matsumura , Y. and Yoshikoshi , A. 1981 . J. Amer. Chem. Soc. , 103 : 2434 For use of this trifunctional starting material in the total synthesis of Siccanin see
- Rajagopalan , S. and Raman , P. V. A. 1955 . Org. Syn. Coll. , Vol. III : 425
- Gardner , P. D. , Rand , L. and Haynes , G. R. 1956 . J. Amer. Chem. Soc. , 78 : 3425
- Lukes , R. M. , Poos , G. I. and Sarett , L. H. 1952 . J. Amer. Chem. Soc. , 74 : 1401
- The elemental analysis4 reported for ketal 4 is in good accord for a ketal/ketone mixture
- Smissman , E. E. , Chien , P. L. and Robinson , R. A. 1970 . J. Org. Chem. , 35 : 3818 The esterification of a carboxylic acid under ketalization conditions has been observed by. C6H5—CO—CH2CH2CO2H C6H5—C (—OCH2CH2O—)—CH2CH2CO2CH2CH2OH See also D. J. DePasto and M. P. Serve, J. Amer. Chem. Soc., 87, 1515 (1965)
- Ruest , L. , Blouin , G. and Deslongchamps , P. 1976 . Syn. Comm. , 6 : 169
- Hoye , T. R. , Peck , D. R. and Trumper , P. K. 1981 . J. Amer. Chem. Soc. , 103 : 5618 Presumably this occurs via acid-catalized dehydration of 4-oxopimelic acid: See
- Hopff , H. and Griesshaber , H. U. S. Patent #2, 302, 321 . Chem. Abstracts, 37, 2020 (1943)
- German Patent #2, 136, 886 . Chem. Abstracts, 78, 111, 114v (1973)
- Heating the reaction to temperatures in excess of 200°C results in substantial sublimation of succinic anhydride which causes considerable mechanical problems