Thermal Rearrangement of 3-Allyloxy-1,2-Benzisothiazole 1,1-Dioxides: An Unusual Inversion of Products of Sigmatropic [3,3]-Shift to Give the [1,3]-Isomers †
Free accessResearch articleFirst published online December, 1999
Thermal Rearrangement of 3-Allyloxy-1,2-Benzisothiazole 1,1-Dioxides: An Unusual Inversion of Products of Sigmatropic [3,3]-Shift to Give the [1,3]-Isomers †
3-Allyloxy-1,2-benzisothiazole 1,1-dioxides 4 isomerize thermally to give [3,3]- and [1,3]-products 5, 6 of sigmatropic shift, of which the former reacts further to give solely the [1,3]-isomer.
References
1.
CristianoM. L. S. and JohnstoneR. A. W., J. Chem. Soc., Perkin Trans. 2, 1997, 489.
2.
CristianoM. L. S. and JohnstoneR. A. W., J. Chem. Res. (S), 1997, 164.
3.
GriecoP. A., ClarkeJ. D. and JagoeC. T., J. Am. Chem. Soc., 1991, 113, 5488.
4.
GriecoP. A., BrandesE. B., McCannS. and ClarkJ. D., J. Org. Chem., 1989, 54, 5489; GriecoP. A., Aldrichim. Acta, 1991, 24, 59.
5.
CristianoM. L. S., Ph.D. Thesis, University of Liverpool, 1994, p. 109.
6.
AlvesJ. A. C., BarkleyJ. V., BrigasA. F. and JohnstoneR. A. W., J. Chem. Soc., Perkin Trans. 2, 1997, 669.
7.
ZieglerF. E., Chem. Rev., 1998, 88, 1423.
8.
HettlerH., Adv. Heterocycl. Chem., 1973, 15, 264.
9.
MarvellE. N. and SchatzB., Tetrahedron Lett., 1967, 67.
10.
StewartJ. J. P., MOPAC 6.00, QCPE No. 455; supplied by CAChe Work Systems v. 3.0, Oxford Molecular, Oxford Science Park, Oxford OX4 4GA, UK.
