GEMINAL SUBSTITUENT EFFECTS .2. DEPENDENCE OF ANOMERIC STABILIZATION ON STRUCTURE IN ACETALS

被引：26

作者：

BECKHAUS, HD

DOGAN, B

VEREVKIN, S

HADRICH, J

RUCHARDT, C

机构：

[1] UNIV FREIBURG,INST ORGAN CHEM & BIOCHEM,ALBERTST 21,W-7800 FREIBURG,GERMANY

[2] VV KUIBYSHEV POLYTECH INST,KUIBYSHEV,USSR

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1990年 / 29卷 / 03期

关键词：

D O I：

10.1002/anie.199003201

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Quantitative statements about the anomeric effect in acetals 1 were possible through group increments which were derived for the key‐C‐atom by comparison of the bonding enthalpies in acetals, ethers, and hydrocarbons. The extra stabilization by the second oxygen substituent is surprisingly large and is strongly substituent‐dependent [(alkylphe‐nylketoneacetal −12.1, formaldehydeacetal −3.3 kcal mol−1)]. (Figure Presented.) Copyright © 1990 by VCH Verlagsgesellschaft mbH, Germany

引用

页码：320 / 321

页数：2

共 15 条

[1]

[Anonymous], 1970, THERMOCHEMISTRY ORGA

[2] APPLICATION OF FORCE-FIELD CALCULATIONS .4. A FORCE-FIELD FOR THE CALCULATION OF THE STRUCTURES AND HEATS OF FORMATION OF ALKYLBENZENES AND ITS TEST OF RELIABILITY ON HIGHLY STRAINED DIPHENYLETHANES [J].