Bis- and tris(diazomethyl)phosphanes - new building blocks for the synthesis of phosphorus heterocycles

✍ Scribed by Harald Keller; Manfred Regitz

• Publisher: Elsevier Science
• Year: 1988
• Tongue: French
• Weight: 234 KB
• Volume: 29
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)82483-1

✦ Synopsis

The bisand tris(diazomethyl)phosphanes 5 and12 , obtained by electrophilic diasoalkane substitution of 4 or PC13 with lithiated 3 , are starting materials for complicated, heteroatom-substituted compounds. Thus, [3+2]-cycloadditions with the phosphaalkyne 9 and subsequent [1,5]-Tms shifts give rise to the phosphaneslo and 13 which then condense with phosphorus, arsenic, antimony, silicon, or germanium halides tofurnish heterocycles of the types9,11 , or15 with cleavage of chlorotrimethylsilane. Conor-substituted diazo compounds are rare*: the first phosphino-substituted diazomethane was recently prepared from bis(diisopropylamino)chlorophosphane and diazo(trimethylsilyl)methyllithium3. Compounds of this type, in principle, open up a possibility to study the chemistry of the phosphinocarbenes 2~. Here, the main question is whether these compounds exhibit ylide character according to2B or even behave as the A503-phosphaalkynes2c.