DOI: 10.1039/A607785D
(Paper)
Reference Section for: J. Chem. Res. (S), 1997, 96-97
Reactions of Carbonyl Compounds in Basic Solutions. Part 27.1 Alkaline Hydrolysis of Bridged Benz[de]isoquinolin-1-ones: Torsionally Distorted Lactams
(Note: The full text of this document is currently only available in the PDF Version )
Keith Bowden and Simon P. Hiscocks
Abstract
Rate coefficients have been measured for the alkaline hydrolysis of 2,3-ethanoxy- and 2,3-propanamino-2,3-dihydro-1H-benz[de]isoquino lin-1-ones‡ in 70% (v/v) dimethyl sulfoxide–water at several temperatures and of N,N-dimethyl-1-naphthamide in water: the relative rates of hydrolysis, activation parameters and other studies indicate the importance of the torsional distortion of the lactam nitrogen and steric $lsquo;bulk’ factors in controlling reactivity.
References
- Part 26, K. Bowden and A. Brownhill, J. Chem. Soc., Perkin Trans. 2, in press Search PubMed.
- K. Bowden and K. Bromley, J. Chem. Soc., Perkin Trans. 2, 1990, 2111 RSC and references cited therein.
- G. M. Blackburn, C. J. Skaife and I. T. Kay, J. Chem. Res., 1980, (S) 294; (M) 3650 Search PubMed.
- V. Somayaji and R. S. Brown, J. Org. Chem., 1986, 51, 2676 CrossRef CAS; Q.-P. Wang, A. J. Bennet and R. S. Brown, Can. J. Chem., 1990, 68, 1732 CAS; Q.-P. Wang, A. J. Bennet, R. S. Brown and B. D. Santarsiero, J. Am. Chem. Soc., 1991, 113, 5757 CrossRef CAS.
- H. Slebocka-Tilk and R. S. Brown, J. Org. Chem., 1987, 52, 805 CrossRef CAS; A. J. Bennet, Q.-P. Wang, H. Slebocka-Tilk, V. Somayaji and R. S. Brown, J. Am. Chem. Soc., 1990, 112, 6383 CrossRef; H. Slebocka-Tilk, A. J. Bennet, J. W. Keillor, R. S. Brown, J. P. Guthrie and A. Jodham, J. Am. Chem. Soc., 1990, 112, 8507 CrossRef CAS; H. Slebocka-Tilk, A. J. Bennet, H. J. Hogg and R. S. Brown, J. Am. Chem. Soc., 1991, 113, 1288 CrossRef CAS; R. S. Brown, A. J. Bennet and H. Slebocka-Tilk, Acc. Chem. Res., 1992, 25, 481 CrossRef CAS.
- J. von Braun, Ber. Dtsch. Chem. Ges., 1904, 37, 2678.
- R. Sato, K. Oikawa, T. Goto and M. Saito, Bull. Chem. Soc. Jpn., 1988, 61, 2238 CAS.
- K. Bowden and R. S. Cook, J. Chem. Soc. B, 1971, 1765 RSC.
- K. Bowden and K. Bromley, J. Chem. Soc., Perkin Trans. 2, 1990, 2103 RSC.
- C. A. Bunton, B. Nayak and C. O'Connor, J. Org. Chem., 1968, 33, 572 CrossRef CAS.
- H. Maskill, The Physical Basis of Physical Organic Chemistry, Oxford University Press, Oxford, 1985 Search PubMed.
- H. B. Bürgi, J. D. Dunitz and E. J. Shefter, J. Am. Chem. Soc., 1973, 95, 5065 CrossRef CAS.
- Nemesis v1.1, Interactive Molecular Modelling, Oxford Molecular, Oxford, 1991.
- K. Bowden and A. M. Last, J. Chem. Soc., Perkin Trans. 2, 1973, 358 RSC; K. Bowden and F. A. El Kaissi, J. Chem. Soc., Perkin Trans. 2, 1977, 526 RSC; F. Anvia, K. Bowden, F. A. El Kaissi and V. Saez, J. Chem. Soc., Perkin Trans. 2, 1990, 1809 RSC.