SOME DERIVATIVES OF 4-t-BUTYLCYCLOHEXYL AND 1-MENTHOL-PHOSPHOROCHLORIDATES

Abstract

cis and trans-4-t-Butylcyclohexanol and 1-menthol have been converted to the phosphorodichloridates with phosphorus oxychloride. Similar reaction with thiophosphoryl chloride afforded the phosphorodichloridothioates. By using 2 mol equivs. of 4-r-butylcyclohexanol, analogous condensations gave the corresponding phosphochloridates and chloridothioates, but with 1-menthol the reaction was unsuccessful. The various chloridates were characterized by preparation of a wide range of derivatives, e.g. amidates, azides, hydrazides, and hydrazones. These compounds are of interest as potential pesticides and their spectral features are discussed.

Jacobsen Enantioselective Hydrolysis of Glycidyl Diethyl Phosphate

“…Analysis of the diastereomeric composition of (R)-II: To a solution of 0.068 g of menthyl phosphorodichloridite prepared according to [9] in 0.5 ml of THF, we added under dry nitrogen atmosphere at 5oC 0.05 g of pyridine. The mixture was kept for 20 min at 5oC, and 0.064 g of the test diol dissolved in 0.5 ml of THF was added.…”

Phosphorus-31 nuclear magnetic resonance data for some compounds containing alicyclic or heterocyclic substituents

“…Evidence that the nitrile nitrogen rather than the amino theoretical values were obtained and submitted for review. 6 The triphenyltin halide and diorganocyanamide (1/1 mole ratio) were refluxed in acetonitrile for the indicated reaction time. c Based on material that melts within 5 °C of the analytical sample.…”

“…Numerous organophosphorus compounds are well-established pesticides (1). Recently, the synthesis and the reactivity of alicyclic and heterocyclic phosphorochloridates have been studied in some detail with a view to establishing their suitability as potential pesticides (2,(5)(6)(7)(8). In this paper, we present phosphorus-31 NMR data for derivatives of these types of compounds.…”

“…Table II summarizes data for some related thiophosphoryl derivatives; the chemical shifts are in the range normally as- 10.9,d-0.9 a All compounds in this and subsequent tables were measured in deuteriochloroform solutions. 6 References in this and subsequent tables give details of the preparation of the compounds. c See Figure 1 IV.…”