279669-08-8

Upstream product

• 2428-06-0 2-chloro-5,5-dimethyl-[1,3,2]dioxaphosphinane 
• 104-55-2 3-phenyl-propenal 
• 4090-60-2 5,5-dimethyl-1,3-dioxaphosphorinan-2-oxide 
• 279669-06-6 2-(1-hydroxy-3-phenylprop-2-enyl)-5,5-dimethyl-1,3,2-dioxaphosphinane 1-oxide 

Relevant academic research and scientific papers

Chlorophosphonates: Inexpensive precursors for stereodefined chloro- substituted olefins and unsymmetrical disubstituted acetylenes

New chlorophosphonates bearing a 1,3,2-dioxaphosphorinane ring which are useful for the stereospecific synthesis of 5-chlorofurfuryl substituted olefins and chloro-substituted dienes have been obtained by an easy, inexpensive route. The utility of some of these in the synthesis of ferrocenyl- and anthracenyl-substituted unsymmetrical acetylenes has been explored. The structures of the phosphonates (OCH2CMe2CH2O)P(O)CH2(C4H2ClO) (4) and (OCH2CMe2CH2O)P(O)(CH=CHCH(Cl)Ph (7) have been determined; in addition, the stereochemistry of (5-chlorofurfuryl)CH=CH(4-ClC6H4) (13b) and 2,4- Cl2C6H3-CH=CH-CH=C(Ph)Cl (14a) is unambiguously proved by the X-ray structure determination.

Direct synthesis of α-substituted phosphonates

The α-substituted phosphonates (OCH2CMe2CH2O)P(O)CH(X)(Ar) [X=Cl, OMe, NMe2 and OSiMe3], useful precursors for Horner-Wadsworth-Emmons reactions, are readily prepared by treating (OCH2CMe2CH2O)PX with an aromatic aldehyde. In the reaction of (OCH2CMe2CH2O)PCl with furfuraldehyde and cinnamaldehyde, the 5-chlorofurfurylphosphonate (OCH2CMe2CH2O)P(O)CH2 (5-Cl-C4H2O) and the γ-chlorophosphonate (OCH2CMe2CH2O)P(O)CH=CH-CH(Cl)Ph, respectively, are formed in good yields.