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1,3-Dithiolane

Topic: Chemistry

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1,3-Dithiolane
Names
IUPAC name
1,3-Dithiolane
Identifiers
3D model (JSmol)
102455
ChEBI
82036
UNII
Properties
C3H6S2
Molar mass 106.20 g·mol−1
Related compounds
Related compounds
 Ethane-1,2-dithiol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Tracking categories (test):

1,3-Dithiolane is the organosulfur compound with the formula CH
2S
2C
2H
4. Also classified as a heterocycle related cyclopentane by replacing two methylene bridges (-CH2- units) with thioether groups. It is an isomer of 1,2-dithiolane.[1]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 RCHS
2C
2H
4. They are obtained by treating an aldehyde with 1,2-ethanedithiol.[2] Related compounds with the formula R
2CS
2C
2H
4 are obtained by condensation of 1,2-ethanedithiol with ketones.[3] The dithiolane protected aldehydes and ketones are amenable to many reactions without perturbing the dithiolane ring.[4]

Protecting a carbonyl group by converting it to a 1,3-dithiolane, using 1,2-ethanedithiol
Protecting a carbonyl group by converting it to a 1,3-dithiolane, using 1,2-ethanedithiol

Dithiolanes can often be reverted, i.e., deprotected,[5] to the parent aldehyde and ketone. A variety of reagents have been developed for that purpose.[6]

Reactions

1,3-Dithiolanes derived from aldehydes can be deprotonated:

RCHS
2C
2H
4 + BuLi → RCLiS
2C
2H
4 + BuH

These organolithium compounds degrade with loss of ethylene to give the dthiocarboxylate:

RCLiS
2C
2H
4 → RCS
2Li + C
2H
4

In contrast, 2-lithio-1,3-dithianes (RCLiS
2C
3H
6) are long-lived.

1,3-Dithiolanes are susceptible to a variety of degradation processes involving organometallic reagents leading to other organosulfur compounds.[2][3]

References

  1. ↑ Teuber, Lene (1990). "Naturally Occurring 1,2-Dithiolanes and 1,2,3-Trithianes. Chemical and Biological Properties". Sulfur Reports 9 (4): 257–333. doi:10.1080/01961779008048732. 
  2. ↑ 2.0 2.1 Ni, Zhi-Jie; Luh, Tien-Yau (1992). "Nickel-Catalyzed Silylolefination of Allylic Dithioacetals: (E,E)-Trimethyl(4-Phenyl-1,3-Butadienyl)Silane". Organic Syntheses 70: 240. doi:10.15227/orgsyn.070.0240. 
  3. ↑ 3.0 3.1 Wilson, S. R.; Georgiadis, G. M. (1983). "Mercaptans from Thioketals: Cyclododecyl Mercaptan". Organic Syntheses 61: 74. doi:10.15227/orgsyn.061.0074. 
  4. ↑ Dahnke, Karl R.; Paquette, Leo A. (1993). "2-Methylene-1,3-Dithiolane". Organic Syntheses 71: 175. doi:10.15227/orgsyn.071.0175. 
  5. ↑ Wuts, P. G. M.; Greene, T. W. (2006). Greene's Protective Groups in Organic Synthesis. NY: J. Wiley. doi:10.1002/0470053488. ISBN 9780470053485. 
  6. ↑ Banerjee, Ajoy K.; Laya, M. S. (2000). "Reagents for the preparation and cleavage of 1,3-dithiolanes". Russian Chemical Reviews 69 (11): 947–955. doi:10.1070/rc2000v069n11abeh000583. Bibcode: 2000RuCRv..69..947B. 




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