Symmetrical spiro-phosphoroheterocycles from the selenation of carbohydrazides

Guoxiong Hua; David B. Cordes; Yang Li; Alexandra M. Z. Slawin; J. Derek Woollins

doi:10.1016/j.tetlet.2011.04.058

Symmetrical spiro-phosphoroheterocycles from the selenation of carbohydrazides

Guoxiong Hua
, David B. Cordes
, Yang Li
, Alexandra M. Z. Slawin
, J. Derek Woollins

Research output: Contribution to journal › Article › peer-review

Abstract

2,4-Bis(phenyl)-1,3-diselenadiphosphetane-2,4-diselenide (Woollins' reagent) reacts with benzoic hydrazides in refluxing toluene to give new symmetrical spiro heterocycles in 48-76% isolated yields. However, under identical conditions, treating Woollins' reagent with thiophene-2-carbohydrazide leads to an additional product, 1,3,4-selenadiazole (27% yield) together with the spiro phosphorus heterocycle in 44% yield. Three representative X-ray structures are reported. (C) 2011 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	3311-3314
Number of pages	4
Journal	Tetrahedron Letters
Volume	52
Issue number	26
DOIs	https://doi.org/10.1016/j.tetlet.2011.04.058
Publication status	Published - 29 Jun 2011

Keywords

Phosphorus
Selenium
Heterocycle
Woollins' reagent
X-ray structure
Spiro compounds
MOLECULAR STRUCTURE
CRYSTAL-STRUCTURES
HETEROCYCLES
REACTIVITY

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@article{73aa584af5fc412ebabc2782306bfc62,

title = "Symmetrical spiro-phosphoroheterocycles from the selenation of carbohydrazides",

abstract = "2,4-Bis(phenyl)-1,3-diselenadiphosphetane-2,4-diselenide (Woollins' reagent) reacts with benzoic hydrazides in refluxing toluene to give new symmetrical spiro heterocycles in 48-76\% isolated yields. However, under identical conditions, treating Woollins' reagent with thiophene-2-carbohydrazide leads to an additional product, 1,3,4-selenadiazole (27\% yield) together with the spiro phosphorus heterocycle in 44\% yield. Three representative X-ray structures are reported. (C) 2011 Elsevier Ltd. All rights reserved.",

keywords = "Phosphorus, Selenium, Heterocycle, Woollins' reagent, X-ray structure, Spiro compounds, MOLECULAR STRUCTURE, CRYSTAL-STRUCTURES, HETEROCYCLES, REACTIVITY",

author = "Guoxiong Hua and Cordes, \{David B.\} and Yang Li and Slawin, \{Alexandra M. Z.\} and Woollins, \{J. Derek\}",

year = "2011",

month = jun,

day = "29",

doi = "10.1016/j.tetlet.2011.04.058",

language = "English",

volume = "52",

pages = "3311--3314",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier",

number = "26",

}

TY - JOUR

T1 - Symmetrical spiro-phosphoroheterocycles from the selenation of carbohydrazides

AU - Hua, Guoxiong

AU - Cordes, David B.

AU - Li, Yang

AU - Slawin, Alexandra M. Z.

AU - Woollins, J. Derek

PY - 2011/6/29

Y1 - 2011/6/29

N2 - 2,4-Bis(phenyl)-1,3-diselenadiphosphetane-2,4-diselenide (Woollins' reagent) reacts with benzoic hydrazides in refluxing toluene to give new symmetrical spiro heterocycles in 48-76% isolated yields. However, under identical conditions, treating Woollins' reagent with thiophene-2-carbohydrazide leads to an additional product, 1,3,4-selenadiazole (27% yield) together with the spiro phosphorus heterocycle in 44% yield. Three representative X-ray structures are reported. (C) 2011 Elsevier Ltd. All rights reserved.

AB - 2,4-Bis(phenyl)-1,3-diselenadiphosphetane-2,4-diselenide (Woollins' reagent) reacts with benzoic hydrazides in refluxing toluene to give new symmetrical spiro heterocycles in 48-76% isolated yields. However, under identical conditions, treating Woollins' reagent with thiophene-2-carbohydrazide leads to an additional product, 1,3,4-selenadiazole (27% yield) together with the spiro phosphorus heterocycle in 44% yield. Three representative X-ray structures are reported. (C) 2011 Elsevier Ltd. All rights reserved.

KW - Phosphorus

KW - Selenium

KW - Heterocycle

KW - Woollins' reagent

KW - X-ray structure

KW - Spiro compounds

KW - MOLECULAR STRUCTURE

KW - CRYSTAL-STRUCTURES

KW - HETEROCYCLES

KW - REACTIVITY

U2 - 10.1016/j.tetlet.2011.04.058

DO - 10.1016/j.tetlet.2011.04.058

M3 - Article

SN - 0040-4039

VL - 52

SP - 3311

EP - 3314

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 26

ER -

Symmetrical spiro-phosphoroheterocycles from the selenation of carbohydrazides

Abstract

Keywords

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