116944-17-3

Basic information

• Product Name: 5,5-dimethyl-2-oxo-2-(2-propenyloxy)-1,3,2-dioxaphosphorinane
• Synonyms: 5,5-dimethyl-2-oxo-2-(2-propenyloxy)-1,3,2-dioxaphosphorinane
• CAS NO: 116944-17-3
• Molecular Weight: 206.178
• Mol File: 116944-17-3.mol

Chemical Properties

• CAS DataBase Reference: 5,5-dimethyl-2-oxo-2-(2-propenyloxy)-1,3,2-dioxaphosphorinane(CAS DataBase Reference)
• NIST Chemistry Reference: 5,5-dimethyl-2-oxo-2-(2-propenyloxy)-1,3,2-dioxaphosphorinane(116944-17-3)
• EPA Substance Registry System: 5,5-dimethyl-2-oxo-2-(2-propenyloxy)-1,3,2-dioxaphosphorinane(116944-17-3)

Safety Data

• Hazardous Substances Data: 116944-17-3(Hazardous Substances Data)

Upstream product

• 1005-69-2 2-methoxy-5,5-dimethyl-1,3,2-dioxaphosphorinane 
• 598-31-2 1-bromoacetone 
• 110907-85-2 5,5-dimethyl-2-trimethylsilyloxy-1,3,2-dioxaphosphorinane 
• 3019-04-3 iodoacetone 

Relevant articles and documents

Reaction of Cyclic Silyl Phosphites with Haloacetones

The reaction of cyclic silyl phosphites (2) with haloacetones (3) was investigated.When oxirane compounds were used as scavengers of trimethylsilyl halides, cyclic acetonylphosphonates (4) were obtained directly.Treatment of 2-trimethylsilyloxy-1,3,2-dioxaphosphorinane (2a) with bromoacetone (3b) or iodoacetone (3c) in propylene oxide gave 4a in 24 percent and 41 percent yields, respectively.With cyclohexane oxide, the reaction of 2a with 3c in MeCN at reflux gave 4a in 50 percent yield.Treatment of 5,5-dimethyl-2-trimethylsilyloxy-1,3,2-dioxaphosphorinane (2b) with 3c in the same manner gave 4b in 43 percent yield.Keywords - cyclic silyl phosphite; haloacetone; cyclic acetonylphosphonate; enolphosphate; Arbuzov reaction; Perkow reaction; carbonyl adduct; trimethylsilyl halide scavenger

Reaction of Cyclic Phosphites with Haloacetones

Treatment of various cyclic phosphites (1), e.g.,2-methoxy-1,3,2-dioxaphosphorinane (1a), 2-methoxy-5,5-dimethyl-1,3,2-dioxaphosphorinane (1b) and 2-methoxy-1,3,2-dioxaphosphorane (1c), with haloacetones (2) gave cyclic Arbuzov products (3), cyclic Perkow products (4), cyclic methylphosphonates (5), and acyclic products (6-8).Compound 1a gave all of the products (3a,4a,5a,6ag,7ag,8ag).However, cyclic phosphites with substituents in the ring (1b,1d) gave only the cyclic products (3-5).The five -membered ring phosphite (1c) yielded only the acyclic products (6cg, 7cg).Treatment of 1a with chloroacetone gave only the Perkow products (4a,7ah).Cyclic phosphite (1f)with 2-benzyloxy substituenet afforded simply the cyclic products (3a, 4a, 9).A mechanistic interpretation of these reactions is presented. Keywords---cyclic phosphite; haloacetone; cyclic acetonylphosphonate; cyclic enol phosphate; Arbuzov reaction; Perkow reaction