Benzisothiazole-1,1-dioxide and naphtho-1,2-thiazine-1,1-dioxide

Details Benzisothiazole-1,1-dioxide and naphtho-1,2-thiazine-1,1-dioxide Benzisothiazole-1,1-dioxide and naphtho-1,2-thiazine-1,1-dioxide

1977-09-23

1980-03-04

Rollins, Alton D.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

544 33, 544 60, 544 62, 544 80, 544111, 544135, 544357, 544359, 544368, 546188, 546198, 2602433, C07D27506, C07F 718, C07D27902

Patent

active

041916891

ABSTRACT:
This invention relates to certain 3,3-di(4'-OP-carbocyclic aryl)-2,3-dihydrobenz[d]isothiazole-1,1-dioxides (and-2,3-dihydronaphtho[1,8-de]-1,2-thiazine-1,1-dioxides) and to the preparation thereof by reacting (a) at least 2 equivalents of (i) a 4'-OP-carbocyclic aryllithium compound wherein P is a protecting group compatible with organometallic reagents or (ii) a 4'-OP-carbocyclic arylMgE compound wherein P is a protecting group compatible with organometallic reagents and E is chloro, bromo or iodo and (b) 1 equivalent of a compound selected from a 3-chlorobenz[d] isothiazole-1,1-dioxide and a 3-chloronaphtho[1,8-de]-1,2-thiazine-1,1-dioxide to give the corresponding 3,3-di(4'-OP-carbocyclic aryl)-2,3-dihydrobenz[d]isothiazole-1,1-dioxide or the corresponding 3,3-di(4'-OP-carbocyclic aryl)-2,3-dihydronaphtho[1,8-de]-1,2-thiazine-1,1-dioxide, which compounds are useful in the synthesis of phenol and 1-naphthol sulfam(na)-phthaleins employed, for example, as photographic optical filter agents and filter agent precursors.

REFERENCES:
Beilstein, "Handbuch der Organischen Chemie", Trans I, 27, p. 534.
Abramovitch, R. A., J. Chem. Soc., Perkin Transi, 22, pp. 2589-2594, (1974).
Haslam, E., "Protection of Phenols and Catechols", Protective Groups in Organic Chemistry, Plenum Press, N.Y. (1974).

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