Thiocarbonyls. II. Thiofluorenone¹

Abstract

Thiofluorenone 769 2-Amino-4-methyl-5-thioformamidomethylpyrimidine (XI).-To 1.8 g. (0.01 mole) of the hydrochloride of X dissolved in 5 cc. of water and cooled below 15°a solution of 1.2 g. of potassium carbonate in 4.0 cc. of water was added as rapidly as possible with cooling. A solution of 1.2 g. of potassium dithioformate in 3.5 cc. of water was added immediately and the mixture was stirred for four hours at room temperature. The solid material was isolated by filtration and washed with water. The washed product was dissolved in 8 cc. of 50 ( acetic acid and filtered from a small amount of insoluble material. The warm solution was neutralized with ammonium hydroxide (sp. gr. 0.89), cooled, and filtered. The dried solid, which had a slightly green east, weighed 1.3 g. (71%), m. p. 192-198°. After two recrystallizations from water, XI melted at 212-213°.

[2 + 3]‐Cycloadditions of Phosphonodithioformate S‐Methanides with CS, NN, and CC Dipolarophiles

“…9H-Fluorene-9-thione (thiofluorenone) (12a) was prepared by treatment of 9H-fluoren-9-one in EtOH soln. either with a mixed stream of H 2 S and HCl [20] or by heating with Lawesson's reagent in boiling toluene [21].…”

New Studies on [2+3] Cycloadditions of Thermally Generated N‐Isopropyl‐ and N‐(4‐Methoxyphenyl)‐Substituted Azomethine Ylides

“…cis-1-Methyl-2,3-diphenylaziridine (2b) and cis-1-isopropyl-2,3-diphenylaziridine (2c) were prepared by Gabriel×s method according to [11], trans-1-benzyl-2,3-diphenylaziridine (2d) and cis-1-(4-methoxyphenyl)-2,3-diphenylaziridine (2e) were synthesized according to procedures described by Huisgen et al [10] [23]. Thiobenzophenone (6a) was obtained from benzophenone by treatment with Lawesson×s reagent [26], and 9H-fluorene-9-thione (6b) was prepared according to [27] by thionation of 9H-fluorenone with a H 2 S/ HCl mixture at 0 ± 58 in EtOH. Other reagents used in the present study were commercially available.…”

Reactions of Thioketones with Dichlorocarbene

“…passing through mixed streams of H 2 S and HCl gas in the presence of trimethyl orthoformate as catalyst [20] [21]. For the preparation of fluorene-9-thione (2i), a similar procedure was applied [22], and for di(tert-butyl)thioketone (2j) a protocol involving reaction of di(tert-butyl)ketonimine lithium salt with CS 2 was applied [23]. Benzyl(triethyl)ammonium chloride (TEBA) was synthesized from triethylamine and benzylchloride [24].…”