Tosylmethyl isocyanide

Structural formula
General
Surname	Tosylmethyl isocyanide
other names	p -Toluenesulfonylmethyl isocyanide; TosMIC;
Molecular formula	C 9 H 9 NO 2 S
External identifiers / databases
EC number	253-140-1
ECHA InfoCard	100.048.293
PubChem	161915
Wikidata	Q4187186
properties
Molar mass	195.24 g mol −1
Physical state	firmly
Melting point	111–113 ° C (decomposes)
solubility	almost insoluble in water
safety instructions
GHS labeling of hazardous substances danger
H and P phrases	H: 301-311-331
	P: 261-280-301 + 310-311
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Tosyl methyl isocyanide (TosMIC) is a chemical compound . It is also known as the Van Leusen reagent because it can be used, for example, in the Van Leusen reaction for the synthesis of nitriles. In addition, TosMIC can be used to synthesize oxazoles and imidazoles .

properties

TosMIC has on carbon - atom between the isonitrile, and the sulfonyl group acide hydrogen -atoms. TosMIC receives a nucleophilic center there through deprotonation . The isocyanide carbon is an electrophilic center.

synthesis

TosMIC is obtained in a two-step reaction. First, sodium p -toluenesulfinate , formaldehyde and formamide react to form N - (tosylmethyl) formamide , which is then dehydrated with phosphorus oxychloride to form TosMIC.

Further use

TosMIC is also suitable for the synthesis of pyrroles , indoles , 1,2,4-triazoles and thiazoles .

Individual evidence

↑ ^a ^b Tosylmethyl isocyanide data sheet (PDF) from Fisher Scientific , accessed on February 13, 2014.

↑ ^a ^b Data sheet p-Toluenesulfonylmethyl isocyanide, 98% from Sigma-Aldrich , accessed on July 14, 2013 ( PDF ).

↑ Daan Van Leusen, Albert M. Van Leusen: Synthetic Uses of Tosylmethyl Isocyanide (TosMIC) . In: Organic Reactions . tape 57 , no. 3 , 2004, doi : 10.1002 / 0471264180.or057.03 .

^ Jie Jack Li: Name reactions: A collection of detailed mechanisms and synthetic applications , 5th edition, Springer, Heidelberg, 2014, pp. 613–614, ISBN 978-3-319-03979-4 .

↑ TosMIC (PDF; 56 kB).

↑ Otto H. Oldenziel, Daan Van Leusen, Albert M. Van Leusen: Chemistry of sulfonylmethyl isocyanides. 13. A general one-step synthesis of nitriles from ketones using tosylmethyl isocyanide. Introduction of a one-carbon unit. In: The Journal of Organic Chemistry . Vol. 42, No. 19, 1977, pp. 3114-3118 doi : 10.1021 / jo00439a002 .

↑ BE Hoogenboom, OH Oldenziel, AM van Leusen: p-tolylsulfonylmethyl isocyanide in: Organic Syntheses . 57, 1977, p. 102, doi : 10.15227 / orgsyn.057.0102 ; Coll. Vol. 6, 1988, p. 987 ( PDF ).

[fisher-1] Tosylmethyl isocyanide data sheet (PDF) from Fisher Scientific , accessed on February 13, 2014.

[Sigma-2] Data sheet p-Toluenesulfonylmethyl isocyanide, 98% from Sigma-Aldrich , accessed on July 14, 2013 ( PDF ).

[Organic_Reactions-3] Daan Van Leusen, Albert M. Van Leusen: Synthetic Uses of Tosylmethyl Isocyanide (TosMIC) . In: Organic Reactions . tape 57 , no. 3 , 2004, doi : 10.1002 / 0471264180.or057.03 .

[Li-4] Jie Jack Li: Name reactions: A collection of detailed mechanisms and synthetic applications , 5th edition, Springer, Heidelberg, 2014, pp. 613–614, ISBN 978-3-319-03979-4 .

[regensburg-5] TosMIC (PDF; 56 kB).

[6] Otto H. Oldenziel, Daan Van Leusen, Albert M. Van Leusen: Chemistry of sulfonylmethyl isocyanides. 13. A general one-step synthesis of nitriles from ketones using tosylmethyl isocyanide. Introduction of a one-carbon unit. In: The Journal of Organic Chemistry . Vol. 42, No. 19, 1977, pp. 3114-3118 doi : 10.1021 / jo00439a002 .

[7] BE Hoogenboom, OH Oldenziel, AM van Leusen: p-tolylsulfonylmethyl isocyanide in: Organic Syntheses . 57, 1977, p. 102, doi : 10.15227 / orgsyn.057.0102 ; Coll. Vol. 6, 1988, p. 987 ( PDF ).