An unusual direction was found in the condensation of cyclohexanone and its Mannich base, leading to the formation of previously unknown polycyclic spirohydrochromans. The structure of the compounds was confirmed by 13C NMR and mass spectrometry.Carbonyl-containing spirohydrochromans have become available as a result of the discovery of the ability of t~,flunsaturated ketones to enter into dimerization of the 1,4-addition type. Its characteristics and mechanism were discussed in detail in the review [1]. In [2][3][4] it was shown that the Mannich bases of cyclic ketones can act as synthons during their thermal decomposition, vacuum distillation [5][6][7], steam distillation [8], or acetolysis in acetic anhydride in the presence of sodium aceta.te [9, 10]. In view of the prospects concerning the scientific and applied aspects of compounds of this series we continued to develop optimum conditions of synthesis and investigate features of the transformations with regard to the existence of several reaction centers in the molecule.The methods that we proposed for the benzannellated analog The yield of the product amounted to 57-64%, depending on the conditions [boiling the base (II) in toluene in the presence of hydroquinone, boiling the methiodide of (II) in DMFA with 40% potassium hydroxide, or steam distillation of the hydrochloride of (II)].Compound (I) was oximated in order to confLrm the presence of the C------O group in the molecule. Here it was established that the direction of the reaction was determined by the order in which the reagents (NH2OH.HCI, KOH) were added. If hydroxylamine hydrochloride is added to a water-alcohol alkaline solution of the dimer of (I), the oxime (llI) is formed. Addition of the reagents in the reverse order leads to the formation of 2, 16-dioxatetracyclo[7.6.1.03,8.01,11]hexadecan_ 3-ol (IV) with a 64 % yield.

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It is known [1-3] that derivatives of cycloalka[b]chalcogenopyrylium salts are used as dyes in passive switches of optical quantum generators OQG [3], are used in photocompositions without silver salts [4], and exhibit biological activity [2]. Earlier we demonstrated that cycloalka[b]chalcogenopyrylium salts containing a γ-methyl group in the heterocycle and an α-methylene group in the alicycle react with aromatic aldehydes under harsh conditions at 100°C in a 1:3 mixture of acetic acid and acetic anhydride and form quantitative yields of the corresponding arylidene derivatives [1]. O Ph R O R + A + -A -1a,b 2a,b 1 A = BF 4 ; 2 A = ClO 4 ; 1,2 a R = H, b R = Ph __________________________________________________________________________________________ 1 Saratovorgsintez, Saratov 410059, Russia. 2 N. I. Vavilov Saratov

Properties and Anti-Phage Activity of Fused Hydro(thio)chromans and Their Copper Complexes.-Treatment of readily achieved spiroketone (II) with HCl and H2S results in the formation of fused chroman (III) or thiochroman derivatives (cf. (IV)) which form stable complexes with Cu(II). Some of the synthesized compounds show activity against phage T4. -(FEDOTOVA, O. V.; LIPATOVA, E. V.; KAPITONOVA, E. V.; RESHETOV, P. V.; PLOTNIKOV, O. P.; KHARCHENKO, V. G.; Khim. Geterotsikl.