Thiepan

Structural formula
General
Surname	Thiepan
other names	Hexamethylene sulfide
Molecular formula	C 6 H 12 S
External identifiers / databases
CAS number 4753-80-4 EC number 225-279-8 ECHA InfoCard 100.022.981 PubChem 78493 Wikidata Q180508
properties
Molar mass	116.22 g mol −1
Physical state	liquid
density	0.99 g cm −3 (20 ° C)
Melting point	0.5 ° C
boiling point	173-174 ° C
Refractive index	1.5044 (18 ° C)
safety instructions
GHS hazard labeling no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Thiepan , also known as hexamethylene sulfide , is the simplest sulfur-containing saturated seven-membered heterocycle .

presentation

The representation of thiepane can be prepared by the reaction of 1,6-dibromohexane with sodium sulfide or 1,6-diiodohexane with potassium sulfide effected.

${\displaystyle \mathrm {Br{-}(CH_{2})_{6}{-}Br\ +\ Na_{2}S\longrightarrow \ C_{6}H_{12}S\ +\ 2\ NaBr} }$

properties

Thiepan boils at 173-174 ° C and has a density of 0.99 g / cm ³ .

Reactions

The possible reactions are largely limited to reactions at the sulfur atom and its α-position, the carbon next to the sulfur. Thiepan can be oxidized to sulfones with potassium permanganate or to sulfoxides with hydrogen peroxide .

Leaving groups can also be introduced at α-carbon . Thus, the reaction with N -chlorosuccinimide gives 2-chlorothiepan. This enables further reactions with nucleophiles . For this purpose, for example, Grignard reagents can be used to introduce organic residues.

Sequence of chlorination with N -chlorosuccinimide and Grignard reaction . R = organic radical, X = halide

Individual evidence

1. ↑ ^{a b} Mueller in: MONTHS. Chem. 1953 , 84 , 1206-1214.
2. ↑ ^{a b} David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-484.
3. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
4. ↑ A. Singh, A. Mehrotra, SL Regen: High Yield Medium Ring Synthesis of Thiacycloalkanes , in: Synth. Commun. 1981 , 11 , 409-412.
5. ↑ J. v. Braun: About cyclic sulfides , in: Chem. Ber. 1910 , 43 , 3220-3226.
6. ↑ GW Gokel, HM Gerdes, DM Dishong in: J. Org. Chem. 1980 , 45 , 3634-3639.
7. ↑ RL Crumbie, DD Ridley in: Aust. J. Chem. 1981 , 34 , 1027-1035.
8. ^ HJ Gais in: Angew. Chem. 1977 , 89 , 201-202.
9. ↑ H. Sashida, T. Tsuchiya in: Heterocycles 1982 , 19 , 2147-2150.