Synthesis of Some Novel Racemic 1, 1\ –Binaphthyl Derivatives Having Photochemical Applications

Abstract

The original work will be presented in the following sequence: Synthesis of some new binaphthyl derivatives using β-naphthol to give 2, 1`-bi-2-naphthol (BINOL) which is versatile and readily obtainable substance.Recently,its chemistry has received much attention in the chemical literature owing to their high activity towards bacteria and fungi as well.Also,they have photochemical applications, such compounds are proved to be important to detect some hazardous waste in particular mercuric (Hg+2) containing compounds. BINOL reacted with allyl bromide and phenylisothiocyanate, also BINOL and iodoBINOL reacted with acetyl chloride,benzoyl chloride and phenylisocyanate to give BINOL derivatives which have various biological activities.(C.f. Scheme 1,2).

Scheme 1

Also BINOL reacted with different types of dibromoalkanes to afford different derivatives having positive effect on bacteria and fungi. (C.f. Scheme 3).

Scheme 3 Also BINOL reacted with chloroacetonitril,benzylchloride and its derivatives to give different products having high biological activity. (C.f. Scheme 4).

Scheme 4 BINOL also can afford benzophenoxazin derivatives (24) through reaction with zinc complex which has unexpected photochemical applications (C.f. Scheme 5). The structures of all formed compounds were characterized by different spectroscopic tools such as (IR, 1HNMR, MS and U.V). Scheme 5 List of New Compounds 1-(2-hydroxynaphthalen-1-yl) naphthalen-2-ol (2) 3, 3`-diiodo-1, 1`-binaphthalenyl-2, 2`-diol (3) 2-(allyloxy)-1-(2-(allyloxy) naphthalen-1-yl) naphthalene (4) 1-(2-hydroxynaphthalen-1-yl) naphthalen-2-yl phenylcarbamothioate (5) (1-(2-acetate naphthalen-1-yl) naphthalen-2-yl acetate (6) 1-(2-hydroxynaphthalen-1-yl) naphthalen-2-yl acetate (7) 1-(2-hydroxynaphthalen-1-yl) naphthalene-2-yl -benzoate (8) 1-(2-hydroxynaphthalen-1-yl) naphthalen-2-yl phenylcarbamate (9) 1-(2-hydroxy-3-iodonaphthalen-1-yl)-3-iodonaphthalen-2-yl acetate (10) 1-(2-hydroxy-3-iodonaphthalen-1-yl)-3-iodonaphthalen-2-yl benzoate (11) 1-(2-hydroxy-3-iodonaphthalen-1-yl)-3-iodonaphthalen-2-yl phenylcarbamathioate (12) 2-(bromobutyloxy)-1-(naphthalen-1-yl) naphthalene-2-ol (13) 2-(4-bromobutyloxy)-1-(2-(4`bromobutyloxy) naphthalen-1-yl) naphthalene (14) 1- 2-(6-bromohexyloxy)-1-(naphthalen-1-yl)naphthalene-2-ol (15) 2-(6-bromohexyloxy)-1-(2-(6`-bromohexyloxy) naphthalen-1-yl) naphthalene (16) 1-2-(10-bromodecyloxy)-1-(naphthalen-1-yl)naphthalene-2-ol (17) 3-(1-(2-hydroxynaphthalen-1-yl) naphthalen-2-yloxy)propanenitrile (18)