The Phospha-Bora-Wittig Reaction
نویسندگان
چکیده
We report the phospha-bora-Wittig reaction for direct preparation of phosphaalkenes from aldehydes, ketones, esters, or amides. The transient phosphaborene Mes*P?B–NR2 reacts with carbonyl compounds to form 1,2,3-phosphaboraoxetanes, analogues oxaphosphetane intermediates in classical Wittig reaction. 1,2,3-Phosphaboraoxetanes undergo thermal Lewis acid-promoted cycloreversion, yielding phosphaalkenes. Experimental and density functional theory studies reveal far-reaching similarities between reactions.
منابع مشابه
Mechanism of the Phospha-Wittig–Horner Reaction**
General. All reactions were performed under argon using Schlenk techniques. Diethyl ether and THF were freshly distilled from sodium/benzophenone prior to use. 1 H, 13 C and 31 P spectra were recorded on a 400 MHz and 300 MHz spectrometers. Chemical shifts (ppm) were reported and referenced to the internal signal of residual protic solvent. High resolution mass spectral analyses (HRMS) were per...
متن کاملThe Wittig Reaction
This so-called Wittig reaction has a number of advantages over other olefination methods; in particular, it occurs with total positional selectivity (that is, an alkene always directly replaces a carbonyl group). By comparison, a number of other carbonyl olefination reactions often occur with double-bond rearrangement. In addition, the factors that influence Eand Z-stereoselectivity are well un...
متن کاملUsing the Wittig reaction to produce alkenylcarbaboranes.
This communication reports the first use of the Wittig reaction to produce alkenylcarbaboranes.
متن کاملAn unusual P-P double bond formed via phospha-Wittig transformation of a terminal PO complex.
The terminal phosphorus monoxide complex (OP)Mo(N[(t)Bu]Ar)(3), 1 (Ar = 3,5-Me(2)C(6)H(3)), undergoes an O-for-PSiR(3) metathesis reaction with the niobium phosphinidene complex (i)Pr(3)SiPNb(N[CH(2)(t)Bu]Ar)(3), 2, to generate the oxoniobium complex ONb(N[CH(2)(t)Bu]Ar)(3), 3, and the diphosphenido complex (i)Pr(3)SiPPMo(N[(t)Bu]Ar)(3), 4. The structure of 4, as determined by X-ray crystallogr...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
ژورنال
عنوان ژورنال: Journal of the American Chemical Society
سال: 2021
ISSN: ['0002-7863', '1520-5126', '1943-2984']
DOI: https://doi.org/10.1021/jacs.1c06228