Clayton-Jensen reaction

The Clayton-Jensen reaction is a name reaction in organic chemistry . The reaction was researched by JO Clayton, WL Jensen, LZ Soborovsky, YM Zinovev, MA Englin and Roderich Graf. However, Clayton and Jensen first reported the reaction in 1948.

Overview reaction

The Clayton-Jensen reaction is a direct chlorophosphorization of aliphatic hydrocarbons with the help of oxygen and phosphorus trichloride .

The yield of the reaction is very low due to the contamination by oxidizing phosphorus trichloride. A slightly higher yield can be achieved by using more hydrocarbons.

Reaction mechanism

In the proposed reaction mechanism, the radical reaction starts spontaneously due to traces of an initiator in the hydrocarbon. The hydrocarbon reacts with a chlorine radical to form a hydrocarbon radical.

The formation of the iodine radical is also based on the initiator present. The iodine radical attacks an oxygen molecule. The resulting radical then reacts with phosphorus trichloride to form an intermediate product, which splits off a hypoiodite radical. In the last step there is a termination reaction of the radical, in which it reacts either with a chlorine radical or with a hydrocarbon radical formed in the first step. This creates a mixture of phosphoryl chloride and alkylphosophoryl chloride.

application

The Clayton-Jensen reaction is used in the synthesis of alkyl phosphoryl chloride.

See also

• Clay-Kinnear-Perren Reaction

Individual evidence

1. ↑ ^{a b c d e f} Zerong Wang: Comprehensive Organic Name Reactions and Reagents . John Wiley & Sons, Inc., Hoboken, NJ, USA 2010, ISBN 978-0-470-63885-9 , pp. 673-676 , doi : 10.1002 / 9780470638859 .
2. ^ JO Clayton, WL Jensen: Reaction of Paraffin Hydrocarbons with Phosphorus Trichloride and Oxygen to Produce Alkanephosphonyl Chlorides . In: Journal of the American Chemical Society . tape 70 , no. November 11 , 1948, p. 3880-3882 , doi : 10.1021 / ja01191a103 .
3. ^ Roderich Graf: About the conversion of alkanes with phosphorus trichloride and oxygen . In: Chemical Reports . tape 85 , no. 1 , 1952, pp. 9-19 , doi : 10.1002 / cber.19520850104 .
4. ↑ ^{a b c} Frank R. Mayo, Lois J. Durham, Kyle S. Griggs: The Reaction of Alkanes with Phosphorus Trichloride and Oxygen . In: Journal of the American Chemical Society . tape 85 , no. October 20 , 1963, p. 3156-3164 , doi : 10.1021 / ja00903a023 .
5. ^ A. Furman Isbell, FT Wadsworth: A Study of the Reaction of Hydrocarbons with Phosphorus Trichloride and Oxygen . In: Journal of the American Chemical Society . tape 78 , no. December 23 , 1956, p. 6042–6045 , doi : 10.1021 / ja01604a025 .
6. ↑ WL Jensen, CR Noller: The Preparation of Phosphonyl Chlorides by the Reaction of Hydrocarbons with Phosphorus Trichloride and Oxygen . In: Journal of the American Chemical Society . tape 71 , no. 7 July 1949, p. 2384-2385 , doi : 10.1021 / ja01175a040 .
7. ↑ RL Flurry, Charles E. Boozer: The Mechanism of the Chlorophosphonation of Hydrocarbons by Phosphorus trichloride and Oxygen . In: The Journal of Organic Chemistry . tape 31 , no. 7 , July 1966, p. 2076-2083 , doi : 10.1021 / jo01345a008 .