108592-96-7

Upstream product

• 78114-26-8 (2,2-dimethyl-1-(trimethylsiloxy)propylidene)-trimethylsilylphosphine 
• 35431-71-1 3-methyl-4-phenylsydnone 
• 78129-68-7 2,2-dimethylpropylidynephosphine 
• 16965-72-3 dimethyl α-diazobenzylphosphonate 
• 108592-91-2 (3-tert-Butyl-5-phenyl-1H-1,2,4-diazaphosphol-1-yl)phosphonsaeure-dimethylester 
• 108592-78-5 1H-3-phenyl-5-tert-butyl-1,2,4-diazaphosphole 
• 74-88-4 methyl iodide 

Relevant academic research and scientific papers

Phosphorus Compounds with Unusual Coordination, 21. - Cycloaddition of Mesoionic Compounds onto a Stable Phosphaalkyne - New Facilities in the Synthesis of Aza- and Thiaphospholes

1,2,3-Oxadiazolium-5-olates (sydnones) (2a-e) react with the phosphaalkyne 1 under cycloaddition and following cycloelimination of carbon dioxide to give 1H-1,2,4-diazaphospholes 5a-e.Only in the reaction 1 + 2a the regioisomer 6a can also be detected as by-product.Starting with 1H(or 2H)-1,2,4-diazaphospholes some representatives of the same series are accessible by lithiation and subsequent methylation (7a-c -> 8a-c -> 5a,c,e).The 1,3-oxazolium-5-olate (muenchnone) 12 as well as the 1,3-dithiolium-4-olate 14 react analogously with 1 to yield the 1,3-aza- and 1,3-thiaphosphole 13 and 15, respectively.Constitutional isomeric thiazaphospholes (17, 18) are formed in the reaction of 1 with the 1,2,3-oxathiazolium-5-olate 16.

Phosphorus Compounds with Unusual Coordination, 19. - 1,2,4-Diazaphospholes by Cycloaddition of Diazo Compounds onto a Stable Phosphaalkyne

Diazomethyl compounds (2a-h) add regiospecifically onto the phosphaalkyne 1 to the adducts 3 which isomerize by spontaneous H-shift to the 1,2,4-diazaphospholes 4a-h.Onty at the reaction 2i+1 the H-shift is suppressed in favour of a trimethylsilyl migration (->6i).Also at the addition of α-diazo ketones 7a-e onto 1 the primary adducts 8 cannot be isolated as they isomerize by fast acyl-shift to N-acceptor-substituted diazaphospholes (9a-e).In the case of 7a-c parallel to that formation of isomers (11a-c) can be demonstrated.The corresponding reaction sequence of the phosphaalkyne 1 with cyclic α-diazo ketones (12, 14, 16, 18) makes easily accessible annelated representatives of the same structural type (13, 15, 17, 19).Phosphoryl group migrations are responsible for the formation of phosphorylated 1,2,4-diazaphospholes (24-c) at the reaction 1+20a-c.N-Acyl and -phosphoryl groups of the rearranged cycloadducts are easily solvolysed (9a-e -> 4b,c,j,k; 24a-c -> 4b,c; 13 -> 25).