Abstract
The acid hydrolysis of 1 assisted by the neighbouring amide group was kinetically investigated and salt effects were studied; the thermodynamic activation parameters calculated for the acid hydrolysis of other substrates (3–6) indicate that the methyl group in the side chain works on the enthalpic or on the entropic factor depending on the size of ring formed.
Keywords
References
1.
Arcelli A.
,
Porzi G.
, and
Sandri S.
, Tetrahedron 1995 , 51 , 9729
2.
Arcelli A.
,
Papa M.
,
Porzi G.
, and
Sandri S.
, Tetrahedron 1997 , 53 , 10513
3.
Arcelli A.
,
Porzi G.
,
Rinaldi S.
, and
Sandri S.
, J.Chem.Soc. Perkin 2 2001 , 296
4.
Arcelli A.
,
Cecchi R.
,
Porzi G.
,
Rinaldi S.
, and
Sandri S.
, Tetrahedron 2001 , 57 , 4039
5.
Arcelli A.
,
Cecchi R.
,
Porzi G.
,
Rinaldi S.
, and
Sandri S.
, Tetrahedron 2001 , 57 , 6843
6.
Rochester C.H.
, Acidity Functions , Academic Press ; London ; 1970 , pp.21 .
7.
Cookson R.F.
, Chem. Rev. 1974 , 74 , 5, and references therein.
8.
Moore J.W.
, and
Pearson R.G.
, Kinetics, and Mechanism , J.Wiley, and Sons ; New York ; 1981 , p. 272 .
9.
(a)
Bamford C.H.
, and
Tipper C.F.H.
, Comprehensive Chemical Kinetics , Elsevier ; New York ; 1969 , Vol. 2 , 337
10.
Bamford C.H.
, and
Tipper C.F.H.
, Comprehensive Chemical Kinetics , Elsevier ; New York ; 1969 , Vol. 2 , 333
11.
Bamford C.H.
, and
Tipper C.F.H.
, Comprehensive Chemical Kinetics ; Elsevier ; New York ; 1969 , Vol. 2 , 357 .
12.
Schlager L.L.
, and
Long F.A.
, Adv. Phys. Org. Chem. 1963 . 1 , 1 . 12
Lightstone F.C.
, and
Bruice T.C.
, J.Am.Chem.Soc. 1996, 118, 2595