Cyclohexene imides

Uses. The principal commercial appHcation for trichloromethanesulfenyl chloride is as an intermediate for the manufacture of fungicides, the most important being captan (A/-(trichlotomethylthio)-4-cyclohexene-l,2-dicatboximide) [133-06-2] (1) and folpet (/V-(tricblorometbyltbio)pbtba1 imide)... 

V-(trichloTomethylthio)phtha1 imide [133-07-3], andDifolatan, OT-N-[l,l,2,2-(tetrachloroethyl)thio]cyclohexene-l,2-dicarboximide [2425-06-1] (243). 

Als vinyloger Carbonsaure-imid-ester wird l-Athoxy-3-benzylimino-cyclohexen mit Natriumboranat oder Lithiumalanat unter 1,4-Addition in 80%iger Ausbeute ausschlieB-lich zu 1 -Athoxy-3-benzylimino-cyclohexan reduziert4 ... 

Several field experiments were conducted in Costa Rica from 1949 to 1952 by McLaughlin and Bowman (24), in which comparisons were made of Bordeaux mixture at 30- and 60-day intervals and Dithane Z-78 (zinc salt of ethylenebisdithiocar-bamic acid) and SR-406 [captan, n-(trichloromethylthio)-4-cyclohexene-l,2-dicarbox-imide] at 30-day intervals. Bordeaux mixture was found the most effective in reducing infection, but no significant differences were found in yield due to the treatments. Results of 1952 to 1953 experiments (37, 44) showed that Bordeaux mixture and Dithane Z-78 applied every 30 days increased yield in comparison with the other treatments. The yield increase obtained with Dithane might have been due to the presence of zinc in this fungicide and not to a reduction in the incidence of the disease. 

To improve the processability of PI and to alleviate or eliminate volatiles, work began in the late 1960 s under NASA Lewis sponsorship (23), to end-cap oligomers with reactive groups. The first report involved the use of 3,6-endomethylene-l,2,3,6-tetrahy-drophthalic anhydride (5-norbornene-2,3-dicarbo ylic anhydride, nadic anhydride) and alkyl derivatives thereof (e.g. citraconic anhydride) and 1,2,3,4-tetrahydrophthalic anhydride (4-cyclohexene-1, 2-dicarboxylic anhydride) as the reactive end group on imide oligomers (23-25). This initial effort led to the development of P13N [with T for polyimide, 13 for Mn of 1300g/mole and N for nadic end cap] whose structure is shown below. 

Fused ring heterocycles, prepared by cyclization of substrates with a tethered nitrogen nucleophile, have been used in the synthesis of amino sugars and aminocyclitols. The examples shown in Table 28 make use of imidate-type functionality (equation 101) to insure nucleophilic attack by nitrogen. The bro-mocyclization of N,W-dialkylaminomethyl ethers of 2-cyclohexen-l-ol to form bicyclic oxazolidine derivatives has been reported also.228b... 

A-halo electrophiles (TV-halo amines, A-halo amides and iV-halo imides) react with alkenes such as 1-hexene, cyclohexene and styrene in the presence of boron trifluoride to give halofluorides and A-halo adducts (equation 34)51. These types of reactions have been dis-... 

The thermally or photochemically activated addition of cyclic A-bromo imides to alkenes, particularly to cyclohexene, is inefficient, even when diastereoselective63-66,141. However, A-bromo phthalimide reacted readily with 2,3-dihydrofuran to give the regioisomers 2 and 3, and with 3,4-dihydro-2//-pyran to give 4 regioselectively in satisfactory yield141. The franv-diastereomers were formed predominantly, especially in the case of the six-membered cyclic compound 4. 

Af-(l,l,2,2-TETRACHLOROETHYLTHIO)-4-CYCLOHEXENE-l,2-DICARBOX-IMIDE (2425-06-1) Incompatibe with acids or acid vapor. Strong alkaline conditions contribute to instability. 

The photoaddition of A -ethylphthalimide (413) to cyclohexene in methanol affords the two adducts (414) and (415). The incorporation of methanol could result from trapping a radical cation. Such a mechanism has been put forward for the formation of the products (416) and (417) from the phthal-imide derivatives (418). The cyclized products (419, 420) are formed on the irradiation of the phthalimide derivatives (421a—c) in methanol. In the case of... 

The data given in Table 2 show that the ester bonds in the COLs III and IV as well as the cyclic imide group in XIII considerably decrease the epoxidation rate in comparison with non-substituted cyclohexene as well as with cyclohexene compounds bearing substituents other than ester groups. It may be due to the electron acceptor character of the ester group. The presence of two groups (IV) and two carbonyls in the cychc imide XIII decreases the reaction rate even more. 

CAS 133-06-2 EINECS/ELINCS 205-087-0 Synonyms 1 H-lsoindole-1,3(2H)-dione, 3a,4,7,7a-tetrahydro-2-((trichloromethyl) thio)- 1,2,3,6-Tetrahydro-N-(trichloromethylthio) phthalimide N-Trichloromethylmercapto-4-cyclohexene-1,2-dicarbox-imide N-Trichloromethylthio-4-cyclohexene-1,2-dicarboximide N-(Tri-chloromethylthio)cyclohex-4-ene-1,2-dicarboximide N-Trichlorometh-ylthiotetrahydrophthalimide Classification Organic compd. 

Decomposition of the reagent in boiling benzene-cyclohexene affords a quantitative yield of a 3 1 mixture of Imide and enesuT fonamlde (eq 4). ... 

The allylic bromination of cyclohexene was successfully done using co(polyethylene-N-bromomaleimide). When polymeric AT-bromosuccin-imide ( -NBS) was used for bromination of cumene, products other than those of benzylic bromination were also formed (Scheme 12-10) (Yaroslavsky et aL, 1970a,b). The change in mechanism has been attributed to the polar environment provided by neighboring succinimide units in (p)-NBS. Polymeric A/-chloromaleimide, synthesized by Yaroslavsky and Katchalski (1972), on reaction with ethylbenzene, also gave products due to aromatic substitution. 

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