2.4- Dimethylthietane

Ferrets, Mustek furo, distinguish between anal sac secretions of males and females. Males did not discriminate between the anal gland odors of estrous and anestrous females. Chemical sex differences were found, but no seasonal differences. Males had high concentrations of 2,3-dimethylthietane and/or 3,4-dimethyl-l,2-dithiolane (Fig. 7.6). Most individuals had 2-propylthietane. Clapperton etal. (1988) concluded that the odor of the anal gland provides sexual and territorial signals and cues to individual identity. 

Animal Sources. The marine annelid worm Lumbrineris hetero-poda produces an insect toxin nereistoxin, 24, 4-N,N-dimethyl-amino-1,2-dithiolane (5 ). The mink MusteXa vison) affords 2,2-dimethylthietane, 14, and 3,3-dimethy1-1,2-dithiolane, 25 (28,63, 64), the ferret Musteta putoris) secretes 14, 25, cis- and trans-2,3-dimethylthietane, 2-propyl- and 2-pentyl-thietane, cis and trans-3,4-dimethyl-l,2-dithiolane, and 3-propyl-l,2-dithiolane (65), and the stoat (Mustela erminea) contains 2-ethyl-, 2-propyl-, and 2-pentyl-thietane, and 3-ethyl- and 3-propyl-l,2-dithiolane in its anal gland (5, ). These several thiaheterocycles from mustela species probably function as scent markers. 

Dimethylthietane is a component of the secretion from the anal gland of the mink (Mustek vision). the European polecat (M. putorius) and ferret. The ferret also produces cis- and trans-2,3-dimethylthietane, 2-n-propylthietane, and 2-n-pentylthietane. 2-n-propylthietane is the major malodorous substance secreted by the anal gland of the male stoat (M. erminea). The female stoat secretes 2-ethylthietane. Thietane, itself, is said to be a component of shale oil. ... 

DOL 1.3-Dioxolane, OX oxetane, THF tetrahydrofuran. DMT 3.3-Dimethylthietane, MOXZ 2-methyl-2-oxazoline. 

Field mice and Clethrionomys Mink Mustela vison 2,2-Dimethylthietane Avoidance of traps from anal gland Robinson, 1990... 

The European rodents A. sylvaticus and Clethrionomys glareolus tend to avoid traps scented with 2,2-dimethylthietane from the anal sacs of the mink, Mustek vison, while it suppresses feeding in European wild rahhits, Oryctolagus cuniculus (Robinson, 1990). 

X-Ray studies of 2,2-dimethylthietane 1,1-dioxide revealed a nonplanar, rhombic crystal structure without showing any evidence for intra- or intermolecular hydrogen bonding. ... 

The synthesis of 2,2-dimethylthietane—the malodorous anal secretion of the mink—includes a 1,4-elimination of a suitably substituted chlorothiol, which was prepared from l,3-dichloro-3-methylbutane (Eq. 14). 

Unusual fragmentation reactions for thietanium salts have been observed. Their analysis may reveal more information about the influence of d-orbitals in the reaction mechanisms of organosulfur compounds. Alkylation of certain thietanes leads to 5-methylthietanonium salts. The thietanium salt 193, which is formed from 2,4-dimethylthietane and (CH3)30" BF4, breaks up when treated with n-butyllithium into a reactive biradical and its resulting cyclopropane and a thioether. 

The very useful lanthanide shift reagents, which facilitate analysis of molecular stereochemistry because of their line-broadening characteristics in NMR spectra, were studied when bound as a chelate complex to thietanes. X-Ray analysis of the adduct 3,3-dimethylthietane 1-oxide with tris(dipivalo-methanato)europium(III) [Eu(dpm)3] revealed the structure of a seven-coordinate complex (271). ... 

The block copolymer of ethylene oxide and 3,3-dimethylthietane shows useful properties of complexing halogen and heavy metal salts (79MI51402). Thietanes can be polymerized with methylmagnesium iodide as well as with a variety of electrophiles such as methyl sulfate, trimethyloxonium tetrafluoroborate, triethylaluminum, boron trifluoride and phosphorus trifluoride (67IC1461, 67MI51400). Thietane (210) has been patented as a stabilizer for poly(vinyl chloride) (73USP3767615). 

Such a situation prevails in the polymerisation of cyclic sulphides such as 3,3-dimethylthietan,... 

A number of 1,3-episulphides (thietans) have been shown to polymerise readily by cationic means using stable salts as initiators (53). The most studied monomer is 3,3 -dimethylthietan (33,52,53) which gives reasonable rates of... 

Table 10. Rate constants for propagation by free ions (fc ) and ion pairs fc in the polymerisation of 3,3-dimethylthietan (53)...

The reaction of 2,2,4,4-tetramethyl-l,3-cyclobutanedione with tetraphosphorus decasulfide (P4S10) led to ring cleavage and the formation of the intermediate dimethylthioketene, which underwent [2+2] cycloaddition after 12 h in refluxing pyridine to give 4-isopropylidene-3,3-dimethylthietane-2-thione 88 in nearly quantitative yield (Equation 28) <2004BCJ187>. 

Reactions of 4,4-dimethyl-2,5-diphenylisooxazolidine-3-thiones llOa-d with toluene or benzene in the presence of anhydrous aluminium chloride at room temperature led to the formation of 3,3-diaryl-/V-(/>-bi phenyl )-2,2-dimethyl-propanothioamides and 4-aryl-2-[(/>-biphenylimino)]-3,3-dimethylthietanes llla-e in satisfactory yields (Table 10) <1996H(43)1211>. 

The complex compounds such as Eu(DPM)3 with 3,3-dimethylthietane-l-oxide and Lu(DPM)3 with 3-methyl pyridine have been synthesized and the geometries adapted by... 

Substituted and 4,4-Disubstitutcd 3-Dialkylamino-2,2-dimethylthietane 1,1-Dioxides 4 and 5 General Procedure117 ... 

NMR studies of the polymerization of THF, oxepane, 3,3-dimethylthietane, 2-methoxy-2-oxo-l,3,2-dioxaphosphorinane and 2-methyl-2-oxazoline revealed that the structures of the growing qj ies are the corresponding onium ions these structures are given in Table 7 (earlier, the first reaction products, formed upon initiation, were observed in the polymerization of THF ). 

The polymerization of cyclic sulfides and amines provided, although tentatively, some information on kp and kp. The equality k kp was found (the Kq value measured for an initiator used was further applied in the determimtion of a in polymerization studies) in the polymerization of 3,3-dimethylthietane in CgHsNOa and qualitatively for l-phenylmethyl-2-methyl-aziridine Small differences were found between kp and k (the macrocation being less... 

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