34281-40-8Relevant academic research and scientific papers
Reactions of thioketones with dichlorocarbene
Mloston, Grzegorz,Romanski, Jaroslaw,Swiatek, Anna,Heimgartner, Heinz
, p. 946 - 956 (2007/10/03)
The reactions of sterically crowded cycloalkanethiones of type 2 with CHCl3/NaOH under phase-transfer catalysis (PTC) with benzyl(triethyl)ammonium chloride (TEBA) as catalyst afforded the corresponding 'gem.-dichlorothiiranes' of type 3 in good yields (cf. Scheme 2 and Table). The desulfurization, which, in some cases, occurred spontaneously, led to (dichloromethylidene)cycloalkanes of type 4. Similar results were obtained using Seyferth's reagent in boiling benzene. In the case of 2,2,6,6-tetramethylcyclohexanethione, reaction under PTC conditions after 3 h yielded only the corresponding dichloromethylidene derivative; on the other hand, workup after 1 h gave (2,2,6,6- tetramethylcyclohexylidene)methanethione (thioketene 9; Scheme 5).
Synthesis of Substituted Fluorenones and Substituted 3',3'-Dichlorospiro and Their Reactivities
Chew, Warren,Hynes, Rosemary C.,Harpp, David N.
, p. 4398 - 4404 (2007/10/02)
Several novel 9-fluorenones were synthesized and were used as precursors in an attempt to prepare unique substituted 3',3'-dichlorospiro.Several of the thiiranes were unstable and desulfurized during their preparation (7a-d, 11, 12). 3',3'-Dichloro(2,5-dimethoxyspiro (7f) was prepared along with 2,2-dichloro-3,3-bis(4-methoxyphenyl)thiirane (16), and 3',3'-dichloro-10,11-dihydrospirocycloheptane-5,2'-thiirane> (17) all of which were stable at room temperature.A study of the reactivity of fluorenyl-substituted thiiranes and other related thiiranes showed that the extent of aromaticity of the substituents at the 3-position of the thiiranes influences their stabilities.
