1,3-Dithiolane

1,3-dithiolane-2D-skeletal.png 75px Dithiolane23d.png 100px 1,3-Dithiolane 102455 19727 changed chemspider 82036 correct chemspider 1S/C3H6S2/c1-2-4-5-3-1/h1-3H2 correct chemspider MUZIZEZCKKMZRT-UHFFFAOYSA-N correct CAS 4829-04-3 20970 341G58G6YL 38079 correct EBI C1CSCS1 3 6 2 Ethane-1,2-dithiol 1,3-Dithiolane is the organosulfur compound with the formula CH2S2C2H4. Also classified as a heterocycle related cyclopentane by replacing two methylene bridges (\sCH2\s units) with thioether groups. It is an isomer of 1,2-dithiolane.10.1080/01961779008048732 Naturally Occurring 1,2-Dithiolanes and 1,2,3-Trithianes. Chemical and Biological Properties 1990 Teuber Lene Sulfur Reports 9 4 257–333 1,3-Dithiolanes are compounds where one or more H atoms of the parent 1,3-dithiolane are replaced by other groups. These species are more widely studied. Synthesis A common family of 1,3-dithiolanes have the formula RCHS2C2H4. They are obtained by treating an aldehyde with 1,2-ethanedithiol.10.15227/orgsyn.070.0240 free Nickel-Catalyzed Silylolefination of Allylic Dithioacetals: (E,E)-Trimethyl(4-Phenyl-1,3-Butadienyl)Silane Organic Syntheses 1992 70 240 Zhi-Jie Ni Tien-Yau Luh Related compounds with the formula R2CS2C2H4 are obtained by condensation of 1,2-ethanedithiol with ketones.10.15227/orgsyn.061.0074 free Mercaptans from Thioketals: Cyclododecyl Mercaptan Organic Syntheses 1983 61 74 S. R. Wilson G. M. Georgiadis The dithiolane protected aldehydes and ketones are amenable to many reactions without perturbing the dithiolane ring.10.15227/orgsyn.071.0175 free 2-Methylene-1,3-Dithiolane Organic Syntheses 1993 71 175 Karl R. Dahnke Leo A. Paquette center|400px|Protecting a carbonyl group by converting it to a 1,3-dithiolane, using 1,2-ethanedithiol Dithiolanes can often be reverted, i.e., deprotected,Wuts P. G. M. Greene, T. W. 2006 Greene's Protective Groups in Organic Synthesis 10.1002/0470053488 9780470053485 J. Wiley NY 83393227 to the parent aldehyde and ketone. A variety of reagents have been developed for that purpose.10.1070/rc2000v069n11abeh000583 Reagents for the preparation and cleavage of 1,3-dithiolanes 2000 Banerjee Ajoy K. Laya M. S. Russian Chemical Reviews 69 11 947–955 2000RuCRv..69..947B 250918297 free Reactions 1,3-Dithiolanes derived from aldehydes can be deprotonated: RCHS2C2H4 + BuLi -> RCLiS2C2H4 + BuH These organolithium compounds degrade with loss of ethylene to give the dithiocarboxylate: RCLiS2C2H4 -> RCS2Li + C2H4 In contrast, 2-lithio-1,3-dithianes (RCLiS2C3H6) are long-lived. 1,3-Dithiolanes are susceptible to a variety of degradation processes involving organometallic reagents leading to other organosulfur compounds. References External links 1,3-Dithiolane Reactions