endstream endobj 636 0 obj <>/Size 485/Type/XRef>>stream 0000048380 00000 n The diastereoselectivity of this reaction was studied. 0000073045 00000 n The Birch Reduction offers access to substituted 1,4-cyclohexadienes. 0000001806 00000 n 0000004048 00000 n 0000045643 00000 n 0000058459 00000 n [�T2�!�RRR�s�`�200�B,���AB�#4��ii V��� ������A��)���@+���2��2Y2|eT`ȔY�p�aږ��ʖ�*�syW�b��p���Fn���Q��l�X4�20߻r0[ $@�( in a 1,4-relationship. 0000004450 00000 n 0000013064 00000 n 0000063416 00000 n 0000087963 00000 n 0000003424 00000 n 0000110856 00000 n averaged and compared with the 1,3- and the 1,4-diene. 0000077811 00000 n ���Pz�ؿ&�Q���E�*�e�*I�X2�՚*�����R������_�� ��B�)�r�3��uT(-ɍ8���}��8қ��_�� 0000000016 00000 n 0000075686 00000 n %PDF-1.4 %���� 0000066070 00000 n 0000076617 00000 n 0000058939 00000 n 0000096467 00000 n is 2, and between the dienyl carbanion and 1,4-diene is 4/3. 0000041374 00000 n 0000041087 00000 n The reaction is called Birch reduction. 0000073355 00000 n 0000075525 00000 n %%EOF 0000002407 00000 n 60 0 obj<> endobj 0000056400 00000 n Ammonia Free Partial Reduction of Aromatic Compounds Using Lithium Di-tert-butylbiphenyl 0000002962 00000 n startxref 0000009137 00000 n The structure on the left 0000002144 00000 n 0000075285 00000 n 0000113375 00000 n T. J. Donohoe, D. House, J. Org. 0000046766 00000 n 0000058620 00000 n xref 0000001512 00000 n 0000088318 00000 n 0000073203 00000 n %%EOF 0000016648 00000 n 485 153 stable through conjugation, can be rationalized with a simple mnemonic. 0000110600 00000 n (�&9�"#�V�|���:ڴx��%�,��%m�b%_iɿ�@粸' 0000003675 00000 n 62 0 obj<>stream 0000056967 00000 n 2018, 20, 3439-3442. 0000061733 00000 n Subsequent functionalization to incorporate the lipophilic properties of the steroidal core afforded N-substituted perhydro-quinolinols as mimics of the AB-ring system of steroids. 0000058781 00000 n 0000098557 00000 n 0000006717 00000 n 0000057979 00000 n 0000061267 00000 n 0000027385 00000 n 0000017061 00000 n 0000074467 00000 n 0000042032 00000 n ;pWҼ��":��p-�e The reaction involves the reaction of dissolving metals in ammonia with aromatic compounds to produce 1,4-cyclohexadienes. 0000073668 00000 n 0000073987 00000 n 0000088112 00000 n The question of why the 1,3-diene is not formed, even though it would be more stable through conjugation, can be rationalized with a simple mnemonic. 86�;�*!��p (LiDBB) ��C�h��sY;���==-� |��&�zI�m���ͺH���C҃Ok$@��@����n�%�C��Hꎏ��z >Z��$g8~���᚞����8��ɍ}���9EK���7%g�a��c�g&���� ���ZH���Q39�*��ň,c����@)���aHV‰����J���G�����þq�1i����bq�,�n@�=Q:��z��U7�0�0�$�H�F����;��l=�t����" RLsB��.��f�. 0000059882 00000 n 0000113246 00000 n 0000040500 00000 n Myers Reduction Chem 115 R OR' O R H O O OMOM H N CH3 OMOM MOMO H3C O O O � :�q�0��!mQ���vĔ@˃_Ipt y�#�97d�/v�� �%�8��5�K�+�X�.g=*2��e 2002, 67, 5015-5018. 0000001432 00000 n 0000008351 00000 n the most highly substituted double bonds: The effect of electron-withdrawing substituents on the Birch Reduction 0000042953 00000 n 0000057174 00000 n 0000040865 00000 n 485 0 obj <> endobj 0000041871 00000 n 9P�|�gT� 9�7?H&԰|�sL���,#����9���@)w���2�A�-w���j���q\�ǐΜ#�*�����4���+`d`�qH3�׀4'�)@� �m�Aɸk#�fe`P~���������q;@� :-cR 0000073510 00000 n 0 ��C��#`ӳ#���%ٗ"`1���x�g�3�%�M�[Z��- -ِ���P������j^V�ٙK�0��)9*d)Ł} �$�)��+�̫f��V��8흹N �T=�F3�-�^ͺ�V�ξ�w��]T�.N$ �i�$�E�C��� 0000113168 00000 n endstream endobj 61 0 obj<> endobj 63 0 obj<> endobj 64 0 obj<>/Font<>/ProcSet[/PDF/Text]/ExtGState<>>> endobj 65 0 obj<> endobj 66 0 obj<> endobj 67 0 obj<> endobj 68 0 obj<>stream 0000088571 00000 n Reduction of Carboxylic Acids Carboxylic acids, acid halides, esters, and amides are easily reduced by strong reducing agents, such as lithium aluminum hydride (LiAlH 4 ). the least change in electron distribution will be preferred. 0000016379 00000 n x�b```��\�B ���,�\��S ����3}m��Aq�l��u>^a� *H,�jz+�B؇��(1��p�g�*�r�5̹�P�J���`OQ�Љ�=M��JO�g��de�XU�z-���.���Y�)��nq]�U�J�2g 'W�����y-�nf� 0000072040 00000 n 0000112870 00000 n P. Lei, Y. Ding, X. Zhang, A. Adijiang, H. Li, Y. Ling, J. varies. 0000091096 00000 n For example, the reaction of benzoic acid leads to 0000068494 00000 n 0000111079 00000 n The comparison with 0000043859 00000 n 0000039989 00000 n Mechanism of the Birch Reduction. 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