The Journal of Organic Chemistry

Ammonolysis of vicinal acetoxy chlorides

SJ Lapporte, LL Ferstandig

文献索引：Lapporte,S.J.; Ferstandig,L.L. Journal of Organic Chemistry, 1961 , vol. 26, p. 3681 - 3685

被引用次数: 7

摘要

Ammonolyses of vicinal acetoxy chlorides proceed more readily than the related vicinal dichlorides. Surprisingly, in anhydrous ammonia at 220, the principal product is vicinal diol; trans-2-acetoxycyclohexyl chloride giving a 77% yield of cis-1, 2-cyclohexanediol. A reversal occurs with aqueous ammonia; an 81% yield of trans-2-aminocyclohexanol was isolated. The distribution of products is attributed to a competition between ester ammonolysis and ...

Formation of Potentially Prebiotic Amphiphiles by Reaction o...

[Mullen, Lee B.; Sutherland, John D. Angewandte Chemie - International Edition, 2007 , vol. 46, # 22 p. 4166 - 4168]

Regio-selective synthesis of 1, 2-aminoalcohols from epoxide...

[Murugan, Andiappan; Kadambar, Vasantha Krishna; Bachu, Sreekanth; Rajashekher Reddy; Torlikonda, Venkatarao; Manjunatha, Sulur G.; Ramasubramanian, Sridharan; Nambiar, Sudhir; Howell, Gareth P.; Withnall, Jane Tetrahedron Letters, 2012 , vol. 53, # 43 p. 5739 - 5741]

An α-aminomethyl carbanion equivalent via a novel Barbier re...

[Chandrasekhar, Sosale; Sridhar, Malayalam Tetrahedron Letters, 2000 , vol. 41, # 23 p. 4685 - 4688]

Importance of the aromatic ring in adrenergic amines. 5. Non...

[Vincek, William C.; Aldrich, Constance S.; Borchardt, Ronald T.; Grunewald, Gary L. Journal of Medicinal Chemistry, 1981 , vol. 24, # 1 p. 7 - 12]